Month: May 2021

Electric Literature of 149520-94-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-amino-1H-imidazole-4-carboxylate (980 mg, 6.8 mmol) and tert- butyl 2-(2,4-dichloroben2ylidene)-3-oxobutanoate (2.03 g, 6.4 mmol) were dissolved in ethanol (15 mL) and the reaction was heated to 75 C for 16 h. The reaction was concentrated under reduced pressure to obtain a 10: 1 mixture (by EtaPLC) of 6-tert- butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine- 2,6-dicarboxylate and 6-tert~butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8- dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylate (3.07 g, 100% crude yield) as a yellow foam. A small amount of this mixture (350 mg) was purified by silica gel chromatography to obtain 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8- dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (190 mg, 54%) and 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-diliydroimidazo[1,2-a]pyrimidine-3 ,6- dicarboxylate (19 mg, 5.4%) as white solids.[00249] For 2-isomer: 1H NMR (400 MHz, CDCl3) delta 10.19 (br s, 1H), 7.43 (d, J= 2.2 Hz, IH), 7.38 (s, 1H), 7.34 (d, J= 7.2 Hz, 1H), 7.21 (dd, J= 2.2, 7.2 Hz, 1H), 6.67 (s, 1H), 4.29 (m, 2H), 2.57 (s, 3H), 1.34 (t, J= 7.0 Hz, 3H), 1.26 (s, 9H).[00250] HPLC-MS Phenomenex LUNA C- 18 4.6 X 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 4.13 rnin, 98% homogeneity index. [00251] LCMS: Anal. Calcd. for C21H23Cl2N3O4451.11 found: 452.24 (M+H)+. [00252] For 3-isomer: 1H NMR (400 MHz, CDCl3) delta 11.72 (br s, 1H), 7.59 (d, J= 8.4 Hz, 1H), 7.50 (br s, 1H), 7.27 (d, J= 3.5 Hz, 1H), 7.18 (dd, J= 3.0, 8.4 Hz, 1H), 6.91 (s, 1H), 4.16 (m, 2H), 2.44 (s, 3H), 1.41 (s, 9H), 1.26 (t, J= 7.0 Hz, 3H). [00253] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 4.24 min, 99% homogeneity index.[00254] LCMS: Anal. Calcd. for C21H23Cl2N3O4451.11 found: 452.24 (M+H)+. [00255] To a stirred solution of 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7- methyl-5,8-dmydroimidazo[1,2-a]pyrimidrne-2,6-dicarboxylate (191 mg, 0.42 mmol) in acetone (5 mL) was added KMnO4 (66 mg, 0.42 mmol). After 1 h, the reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and extracted with H2O (2x). The organic layer was dried EPO over MgSO4, concentrated under reduced pressure and recrystallized from EtOAc to obtain 6-tert-butyl 2-ethyl 5-(2,4-dicMorophenyl)-7-methylimidazo[1,2-a]pyrimidirie- 2,6-dicarboxylate (107 mg, 57%) as white crystals.[00256] To a stirred solution of 6-tert-butyl 3 -ethyl 5-(2,4-dichlorophenyl)-7- methyl-5,8-dihydroimidazo[l ,2-alpha]pyrimidine-3,6-dicarboxylate (19 mg, 0.04 mmol) in acetone (2 mL) was added KMnO4 (7 mg, 0.04 mmol). After 1 h, the reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and extracted with H2O (2x). The organic layer was dried over MgSO4, concentrated under reduced pressure and purified by silica gel chromatography to obtain 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7- methylimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (14 mg, 74%) as white solid. [00257] For 2-isomer: 1H NMR (400 MHz, CDCl3) delta 7.68 (d, J= 1.8 Hz, 1H), 7.53 (s, 1H), 7.50 (dd, J= 1.8, 7.6 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 4.43 (m, 2H), 2.77 (s, 3H), 1.41 (t, J= 7.2 Hz, 3H), 1.29 (s, 9H). [00258] 13C NMR (500 MHz, CDCl3) 6 163.7, 162.7, 159.8, 147.0, 141.1, 138.5, 138.2, 134.5, 131.4, 130.3, 128.1, 127.8, 119.0, 114.1, 83.8, 61.4, 27.7, 24.3, 14.3. [00259] HPLC-MS Phenomenex LUNA C-18 4.6 X 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 3.89 min, 99% homogeneity index. [00260] LCMS: Anal. Calcd. for C21H21Cl2N3O4449.09 found: 450.11 (M+H)+. [00261] HRMS: Anal. Calcd. for C21H22Cl2N3O4 450.0987 found: 450.0981 (M+H)+.[00262] For 3-isomer: 1H NMR (400 MHz, CDCl3) delta 8.38 (s, 1H), 7.41 (d, J= 1.7 Hz, 1H), 7.41 (m, 2H), 3.98-4.17 (m, 2H), 2.77 (s, 3H), 1.27 (s, 9H), 1.22 (t, J= 7.0 Hz, 3H).[00263] 13C NMR (400 MHz, CDCl3) delta 164.0, 159.1, 158.3, 150.5, 144.4, 142.4, 137.0, 134.8, 131.7, 129.9, 128.9, 126.9, 121.1, 117.6, 83.9, 61.0, 27.5, 23.5, 14.3. [00264] HPLC-MS Phenomenex LUNA C-18 4.6 x 50 mm, 0 to 100% B over 4 minutes, 1 minutes hold time, A = 90% water, 10% methanol, 0.1% TFA, B = 10% water, 90% methanol, 0.1% TFA, RT = 3.89 min, 99% homogeneity index.[00265] LCMS: Anal. Calcd. for C21H21Cl2N3O4449.09 found: 450.20 (M+H)+. EPO [00266] The regiochemistry for the 2- and 3-isomers were unequivocally established by single crystal X-ray analysis for both compounds.

The synthetic route of Ethyl 2-amino-1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/71752; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89250-15-7, name is 4-(1-Methyl-1H-imidazol-5-yl)aniline, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 89250-15-7, SDS of cas: 89250-15-7

Reference Example 32 4-(3-Methyl-3H-imidazol-4-yl)phenylhydrazine 4-(3-Methyl-3H-imidazol-4-yl)phenylamine (430 mg) was dissolved in concentrated hydrochloric acid (4.0 ml), water (2.0 ml) and THF (2.0 ml), and an aqueous solution (2 ml) of sodium nitrite (206 mg) was added dropwise to the mixture under ice-cooling. After stirring for 40 minutes, a concentrated hydrochloric acid solution (3 ml) of tin chloride dihydrate (1.34 g) was added to the mixture, followed by stirring at room temperature for 2 hours. The reaction solution was alkalified by adding aqueous ammonia (28%), chloroform:methanol = 10:1 solution was added to the mixture and then filtered through celite. An organic layer of the filtrate was dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain the title compound (289 mg) as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 3.24 (2H, br s), 3.62 (3H, s), 5.34 (1H, br s), 6.88 (2H, d, J=8.8 Hz), 7.01 (1H, s), 7.24 (2H, d, J=8.8 Hz), 7.47 (1H, s).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3718-04-5, name is 5-Vinyl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 3718-04-5

To a stirred solution of salen ligand (0.23 g, 0.9 mmol, 0.05 eq.) in i-PrOH (15 mL) was added MnCl2 (0.11 g, 0.9 mmol, 0.05 eq.) in anopened flask. After stirring with air bubbling at rt for 10 min, a solutionof SG1 nitroxide (5.09 g, 17 mmol, 1.0 eq.) and 4-vinyl-1H-imidazole 29(1.87 g, 20 mmol, 1.2 eq.) in i-PrOH (25 mL) was added, followed bysolid NaBH4 (0.75 g, 20 mmol, 1.2 eq.) added in small portions below25 C. The mixture was stirred at rt for 5.5 h, and the solvent was removedin vacuo. Then sat. NaHCO3 and CH2Cl2 were added and extractedwith CH2Cl2. The combined organic phase was washed withbrine, dried with MgSO4, and concentrated to afford a crude product asa 1: 1 mixture of diastereoisomers (31P-NMR ratio). The crude was separatedby flash column chromatography (CH2Cl2: MeOH=100: 0 to9: 1) to afford (RR/SS)-4a (1.29 g, 19%) and (RS/SR)-4a (1.38 g, 20%).(RR/SS)-4a: pale yellow solid; m.p.: 36-38 C; Rf=0.35 (CH2Cl2:MeOH=9: 1); 1H NMR (CDCl3, 400 MHz): delta 1.05 (s, 9H), 1.19 (t,J=7.1 Hz, 3H), 1.25 (s, 9H), 1.34 (t, J=7.1 Hz, 3H), 1.70 (d,J=6.6 Hz, 3H), 3.37 (d, J=27.4 Hz, 1H), 3.73-3.87 (m, 1H),3.93-4.07 (m, 2H), 4.07-4.20 (m, 1H), 5.13 (q, J=6.6 Hz, 1H), 6.91 (s,1H), 7.56 (s, 1H); 13C{1H}-NMR (CDCl3, 75 MHz): delta 16.0 (d,J=6.6 Hz), 16.2 (d, J=6.6 Hz), 20.2 (s), 27.5 (s), 30.5 (d, J=6.1 Hz),35.1 (d, J=4.4 Hz), 59.0 (d, J=7.2 Hz), 61.27 (d, J=6.0 Hz), 61.30(s), 69.5 (d, J=139.7 Hz), 73.7 (s), 121.2 (br. s), 134.6 (br. s), 136.2(br. s); 31P{1H}-NMR (CDCl3, 162 MHz): delta 26.45; HRMS (ESI-TOF) m/z:[M+H]+ Calcd for C18H37N3O4P 390.2516; Found 390.2514. (RS/SR)-4a: pale yellow solid; m.p.: 100-102 C; Rf=0.47 (CH2Cl2:MeOH=9: 1); 1H NMR (CDCl3, 400 MHz): delta 1.14 (s, 9H), 1.17 (s, 9H),1.20 (t, J=7.1 Hz, 3H), 1.36 (t, J=7.1 Hz, 3H), 1.62 (d, J=6.6 Hz,3H), 3.48 (d, J=27.9 Hz, 1H), 3.73-3.85 (m, 1H), 3.92-4.09 (m, 2H),4.09-4.21 (m, 1H), 5.11 (q, J=6.6 Hz, 1H), 7.01 (s, 1H), 7.54 (s, 1H);13C{1H}-NMR (CDCl3, 75 MHz): delta 15.9 (d, J=3.3 Hz), 16.0 (d,J=2.8 Hz), 17.6 (s), 27.8 (s), 30.7 (d, J=5.5 Hz), 35.0 (d, J=5.0 Hz),59.4 (d, J=7.7 Hz), 60.8 (s), 61.6 (d, J=6.6 Hz), 69.0 (d,J=138.6 Hz), 70.4 (s), 125.7 (br. s), 130.9 (br. s), 134.8 (s); 31P{1H}-NMR (CDCl3, 162 MHz): delta 27.59; HRMS (ESI-TOF) m/z: [M+H]+Calcd for C18H37N3O4P 390.2516; Found 390.2515.

The synthetic route of 3718-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamasaki, Toshihide; Buric, Duje; Chacon, Christine; Audran, Gerard; Braguer, Diane; Marque, Sylvain R.A.; Carre, Manon; Bremond, Paul; Bioorganic and Medicinal Chemistry; vol. 27; 10; (2019); p. 1942 – 1951;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 89088-69-7 as follows. Quality Control of 1-Methyl-1H-imidazol-4-amine hydrochloride

Intermediate 432-Chloro-7-(2-fluoroethyl)-Lambda/-(l -methyl- lH-imidazol-4-yl)-7H-pyrrolo[2,3-dlpyrimidin-4-amineThe solution of 2,4-dichloro-7-(2-fluoroethyl)-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 44, 600 mg, 2.56 mmol) and 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 523 mg, 3.08 mmol) was added to DIPEA (2686 mul, 15.38 mmol) in ethanol (5859 mul) and the reaction mixture was heated at 90 0C for 24 hours. Additional 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 523 mg, 3.08 mmol) and DIPEA (2686 mul, 15.38 mmol) added to the reaction mixture and the mixture was heated at 90 0C for another 24 hours. The volatiles were removed under reduced pressure to afford a residue, which was dissolved in DCM/MeOH (10%) and washed with water. The organic layer was concentrated in vacuum, followed by purification by reversed phase HPLC (Gilson chromatography, 0%->50% MeCN/0.1% TFA H2O) to yield the title product (454 mg). LCMS: 297 [M+H]+.

According to the analysis of related databases, 89088-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 253453-91-7, name is 2-Chloro-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6953-65-7, name is (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6953-65-7, Application In Synthesis of (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol

A mixture of (5 -chloro- 1 H-benzo [d]imidazol-2-yl)methanol (7a) (500 mg, 2.738mmoles, 1 eq.), 4-bromobutyronitrile (466 mg, 1.15 eq.), cesium carbonate (1.338 g,1.5 eq.) and potassium iodide (45 mg, 0.1 eq.) in acetonitrile (5 mL) was refluxedovernight. The mixture was then cooled and filtered. The filtrate was evaporated under vacuum and the residue was treated with ethyl acetate (30 ml) and brine (20 ml). The separated organic layer was dried (Na2SO4), filtered and the solvent was evaporated under vacuum. The residue was purified by column chromatography (eluent: CH2C12:methanol from 1:0 to 15:1) to yield 732mg (54%) of a mixture containing two regioisomers (5- and 6-chloro derivatives) in a 1/1 ratio. This mixture was further separated by SFC to provide the pure regio-isomer (7b).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; HU, Lili; DEMIN, Samuel, Dominique; VENDEVILLE, Sandrine, Marie, Helene; TAHRI, Abdellah; RABOISSON, Pierre, Jean-Marie, Bernard; WO2015/158653; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 10057-46-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10057-46-2, name is 2-Amino-5-(trifluoromethyl)benzoimidazole, This compound has unique chemical properties. The synthetic route is as follows.

2-(2,3-Dih drobenzofuran-5-yl)-N-(5-(trifluoromethyl)-lH-bcnzo[Patent; 4SC DISCOVERY GMBH; LEBAN, Johann; ZAJA, Mirko; WO2014/202638; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 37619-25-3, name is Methyl 1H-benzo[d]imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 1H-benzo[d]imidazole-4-carboxylate

Step AG2: (1 H-Benzoimidazol-4-yl)-methanolTo a solution of 1 H-Benzoimidazole-4-carboxylic acid methyl ester (Step AG3, 1.0 g, 5.68 mmol) in THF (56.8 mL) under argon was added LiAIH4 (1 M in THF) (6.24 mL, 6.24 mmol), dropwise, causing a yellow coloration and a slight gas evolution. The reaction mixture was stirred at rt for 75 min. The medium was carefully quenched by addition of saturated aqueous NH4CI solution (50 mL). The slurry of aluminium salts was stirred for an hour at rt. The organic supernatant was decanted and the insoluble aluminium salts suspension was extracted with AcOEt (3 x 100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to give a colorless oil (600 mg, 71 %). HPLC/MS (Method A) tR0.64 minute, M+H 149.0 . 1 H NMR (DMSO- d6) Ppm 4.85 (br. s., 2 H) 5.19 (br. s., 1 H) 7.07 – 7.26 (m, 2 H) 7.48 (d, J=7.34 Hz, 1 H) 8.19 (s, 1 H) 12.35 – 12.64 (m, 1 H).

According to the analysis of related databases, 37619-25-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BERST, Frederic; FURET, Pascal; MARZINZIK, Andreas; STAUFFER, Frederic; WO2011/157793; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 30086-64-7, A common heterocyclic compound, 30086-64-7, name is Hexahydro-1H-benzo[d]imidazole-2(3H)-thione, molecular formula is C7H12N2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of cyclic thiourea 4a-e (1 mmol) and di(methylsulfanyl)methylenemalononitrile 5a (0.170 g, 1 mmol) in DMF (3 mL) was stirred at 120 C. Upon completion (3 h monitored by TLC), the solvent was removed by rotary evaporator under vacuum. The afforded orange solid washed by ethyl acetate and dried to give 1.

The synthetic route of 30086-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alizadeh, Abdolali; Vahabi, Amir Hossein; Bazgir, Ayoob; Khavasi, Hamid Reza; Zhu, Zhe; Zhu, Long-Guan; Tetrahedron; vol. 72; 10; (2016); p. 1342 – 1350;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 857070-66-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 857070-66-7 name is (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of x-4 (0.0173 mol) and x-3 (0.026 mol) was stirred at 125C for 4 hours, and then taken up in CH2CI2/CH30H. The organic layer was washed with saturated K2C03 solution, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue (9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 90/10/0. 5; 20-45mum). Two fractions were collected and the solvent was evaporated. Yield: 0.7 g of intermediate x-5 (10%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (2-Chloro-1H-benzo[d]imidazol-6-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58871; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem