Author: Jessica.F

Synthetic Route of 641571-13-3,Some common heterocyclic compound, 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, molecular formula is C12H9F3N2O2, 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.

(VII) (10 g), t-butanol (300 mL), triethylamine (7.9 g) and diphenylphosphoryl azide (11.2 g) were added to a 500 mL reaction flask. The mixture was heated to reflux and refluxed for 16 hours then cooled to room temperature. The solvent was removed by evaporation under reduced pressure. The residue was treated with water (150 mL) and extracted with ethyl acetate (2 x 150 mL). The extracts were combined, washed with brine (150 mL), dried over sodium sulfate and evaporated to remove the solvent under reduced pressure to give the crude product (12.5 g).The above crude product (12.5 g), n-propanol (125 mL), p-xylene (125 mL) and solid sodium hydroxide (7.3 g) were added to a 500 mL reaction flask. The mixture was stirred and the mixture was heated to reflux and refluxed for 30 hours. Stirring was stopped, water (162 mL) was added and the azeotrope was distilled off under reduced pressure. The residue was diluted with water (20 mL), cooled to 0 & lt; 0 & gt; C, stirred slowly for 1 h and filtered. The filter cake was washed with water (2 x 30 mL) and dried in vacuo at 55 C to give 7.1 g of the solid compound (I). The HPLC purity was 98.7% and the overall yield of the two-step reaction was 79.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, its application will become more common.

Reference:
Patent; Esteve Huayi Pharmaceutical Co., Ltd; Zhao, Liqiang; Wang, Zhao; Jiang, Hong; Dong, Jin; Xu, Xiaofei; Zheng, Guorong; (9 pag.)CN105985293; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 45676-04-8, 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. 45676-04-8, name is 1-tert-Butylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The procedure given for the synthesis of [DPCP-(ImidMe)2]Cl2 was followed. Yield: 92%. mp: 170-173 C. 1H NMR (400 MHz, CDCl3): delta 12.00 (s, 2H, imidazole-NCHN), 8.47 (s, 2H, imidazole-NCHCHN), 8.10 (s, 2H, imidazole-NCHCHN), 7.73 (m, 6H, Ph-H), 7.62 (m, 4H, Ph-H), 1.90 [s, 18H, C(CH3)3] ppm. 13C NMR (100 MHz, CDCl3): delta 159.86, 137.69, 134.90, 131.27, 129.76, 129.03, 128.22, 127.61, 122.01, 119.29, 62.83, 30.35 ppm. 31P (161 MHz, CDCl3): delta 41.89 ppm (s).

The synthetic route of 1-tert-Butylimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senkuttuvan; Ramakrishna; Bakthavachalam; Reddy, N. Dastagiri; Journal of Organometallic Chemistry; vol. 723; (2013); p. 72 – 78;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6015817; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 615-16-7, 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. 615-16-7 name is 2-Hydroxybenzimidazole, 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.

General procedure: 4-Bromo-2-(substituted) benzonitrile 5a or 5b (5 mmol) was added to a mixture of 1H-benzo[d]imidazol-2(3H)-one (6) (10 mmol) and Cs2CO3 (10 mmol) in DMF (25.0 ml). After 12 h, 50 ml of ice water was added dropwise. The resulting suspension was filtered, and the filter cake was dried in a vacuum oven. The solid was purified by flash chromatography (50 % ethyl acetate in hexane) to afford 4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(substituted) benzonitrile (7a or 7b). 2-(Trifluoromethyl)-4-(1,2-dihydro-2-oxobenzo[d]imidazol-3-yl) benzonitrile (7a) Yield 62 %; White Solid; mp 232-233 C; IR (KBr) nu max: 3189, 3149 (N-Hstretch), 3072 (C-Harom), 2957, 2895, 2820 (C-Halk), 2230 (C:N), 1720 (C=O), 1611 (N-Hbend), 1575, 1507, 1481, 1439 (C=Carom), 1385, 1319, 1240, 1185, 1127, 1053 (C-Hbend), 1272, 558 (C-CF3) cm-1; 1H NMR (400 MHz, CDCl3, ppm): delta 9.372 (s, 1H, NH), 8.14 (s, 1H, H-2), 8.03 (d, 2H, H-5,H-6), 7.2 (m, 4H, phenyl); 13C NMR (100 MHz, CDCl3, ppm): delta 152.9 (C=O), 139.2 (C4), 135.6 (C6), 133.8, 133.1 (q, J = 65 Hz, C2), 128.5 (C0 1), 127.6 (d, J = 34 Hz, C5), 123.3 (C0 6), 122.8 (C0 3), 122.5 (q, CF3), 121.6 (C), 120.4 (C0 5), 114.8 (CN), 110.0 (C0 2), 108.7 (C0 4), 106.6 (C1); HRMS (ESI): m/z calculated for C15H8F3N3O [M?H]?: 304.06922; Found: 304.069.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Hydroxybenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Elancheran; Saravanan; Choudhury, Bhaswati; Divakar; Kabilan; Ramanathan; Das, Babulal; Devi; Kotoky, Jibon; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 539 – 552;,
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. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 7189-69-7

A solution of 1,1?-sulfonyldiimidazole(119 mg, 0.6 mmol), ethinyl estradiol (9,89 mg, 0.3 mmol), and cesium carbonate (49 mg, 0.15 mmol) in 5 mL of tetrahydrofuran was stirred at 23 C for 18 h, and then was concentrated. The residue was dissolved in 5 mL of ethyl acetate, which was washed sequentially with saturated aqueous ammonia chloride, and brine, dried, concentrated, and then chromatographed on silica with 2:3 ethyl acetate / hexane as the eluant, to provide 116 mg(91%) of 10 as a white solid, mp 168- 170 C : 1H NMR (500 MHz, CDCl3) delta 7.74 (s,1 H), 7.32 (d, 1 H, J = 1.5 Hz), 7.24(d, 1 H, J = 9.5 Hz), 7.17 (s, 1 H), 6.63 (d, 1 H, J = 6.5 Hz),6.60 (d, 1 H, J = 1.5 Hz), 2.80 (d, 2H, J = 4.5 Hz), 2.59 (s, 2 H), 2.39 – 2.28 (m, 2 H), 2.24 – 2.18 (m, 1H), 2.08 – 1.97 (m, 1 H), 1.97 – 1.84 (m, 2 H), 1.84 – 1.59 (m, 3 H), 1.54 -1.22 (m, 4 H), 0.88 (s, 3 H); 13C NMR (126 MHz, CDCl3) delta147.1, 141.2, 139.7, 137.8, 131.4, 127.4, 121.3, 118.6, 118.2, 87.6, 79.9, 74.3, 49.7, 47.2, 43.9, 39.1, 38.9, 32.9, 29.7, 26.9, 26.3,23.0, 12.9; ESI-MS m/z 427.1 MH+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7189-69-7.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, molecular formula is C13H9N3, 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. HPLC of Formula: C13H9N3

5/-/-Benzo[c/]benzo[4,5]imidazo[1 ,2-a] imidazole (15.0 g, 72.4 mmol), 4-iodo- 1 ,1 ‘-biphenyl (20.3 g, 72.4 mmol), K3P04 (46.1 g, 217 mmol) and copper(l) iodide (2.76 g, 14.5 mmol) are suspended in 1 ,4-dioxane (750 ml) under argon. The mixture is degassed and heated up to 100 C while stirring. trans- 1 ,2-Diaminocyclohexane (75 ml) is added and stirring at 100 C is continued for four days. Then, the reaction mixture is cooled to room temperature and 5% ammonia in water (600 ml) is added. The precipitate is filtered off. The solid is washed with 5% ammonia in water, pure water, ethanol and heptane. The crude product is dried in vacuo. A grey powder (23 g, 64.0 mmol, 88%) is obtained. (0201) GC-MS (El, 70 eV) = 359 (100%) Synthesized accordingly are the following products using the respective starting materials (SM):

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28890-99-5, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; STENGEL, Ilona; MAIER-FLAIG, Florian; HARBACH, Philipp; MONTENEGRO, Elvira; LUDEMANN, Aurelie; (0 pag.)WO2019/170691; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1402838-08-7,Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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.

Dimethyl (2-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-2-oxoethyl)phosphate (0207-60) (400 mg, 1.47 mmol, 3.3 eq),2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (180 mg, 0.44 mmol, 1.0 equiv) andCesium carbonate (958 mg, 2.94 mmol, 2.0 eq.)Added to 40 ml of isopropanol,Stir the reaction overnight at room temperature,Concentrate under reduced pressure, add ethyl acetate and water, separate, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain 1-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-) as a yellow solid. 5-base)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (540 mg, crude)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1-Trityl-4-imidazolyl)benzaldehyde, its application will become more common.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 17334-08-6, A common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, molecular formula is C5H8N2O, 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.

To 1.12 g of 1-methyl-2-imidazolemethanol are added dropwise 1.8 ml of thionyl chloride at 0 C. After 18 hours at 20 C., the mixture is heated at 70 C. for 2 hours. The reaction medium is concentrated to give the expected product quantitatively. 1H NMR delta in ppm (DMSO d6): 3.90 (s, 3H); 5.22 (s, 2H); 5.36 (t, 1H); 7.77 (d, 1H); 7.80 (d, 1H).

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:
Patent; SANOFI-AVENTIS; US2007/185136; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

COMPOUND 14. 1.2 : NnN-DIETHYL-4- {6-METHOXY-2-r (5-METHYL-1H- IMIDAZOL-4-YL . METHYL]-7-PHENOXY-1. 2e3. 4- TETRAHYDROISOQUINOLIN-1-YL} BENZAMIDE; To INTERMEDIATE 10.2. 1 (30 mg, 0.06 mmol) was added a solution of hydrochloric acid in 1,4-dioxane (4N, 0.5 mL) at room temperature. The reaction mixture was stirred for an hour then concentrated by a stream of nitrogen and dried under vacuum. The residue was re-dissolved in 1,2-dichloroethane (1.5 mL) and to this solution was added 4-methyl-lH-imidazole-5-carbaldehyde (-2eq, 0.12 mmol, 12 mg) and followed by sodium triacetoxyborohydride (4eq, 0.24 mmol, 50 mg). The reaction mixture was stirred for 20 hr then quenched with saturated aqueous sodium bicarbonate and extracted to dichloromethane (15 mL x 2). Excess aldehyde was removed by stirring the extracted dichloromethane with polymer supported hydrazine for 2 hr. The polymer was filtered off and the filtrate was concentrated and dried under vacuum. Product was purified by flash chromatography, using Si02 column with MeOH/DCM (10: 90) afford 17.9 mg (0.034 mmol, 60%) of COMPOUND 14. 1.2 as light yellow oil. 1H NMR (500 MHz, CDC13): b 1. 05 (br s, 3H), 1.18 (br s, 3H), 2.00 (s, 3H), 2.50-2. 98 (br m, 4H), 3.10 (br s, 2H), 3.28 (m ; 1H), 3.49 (br s, 2H), 3.52 (m, 1H), 3.72 (s, 3H), 4.45 (s, 1H), 6. 28 (s, 1H), 6.65 (s, 1H), 6.68-7. 20 (m, 9H), 7.26 (m, 1H). 13C NMR (125 MHz, CDC13) : 6 10.97, 13.09, 14.42, 28. 70,39. 65, 43. 68, 46.96, 49.24, 56.20, 67. 66,106. 00,112. 63,115. 47,116. 47,122. 02,126. 57, 129.91, 130.26, 131.76, 132.93, 136.34, 142. 69,145. 32, 150.37, 150.37, 171. 51. (+) LRESIMS m/z 525 (M+H) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 2-(1H-Imidazol-1-yl)acetonitrile

Reference Example 9 Using 0.88 g of 1-cyanomethylimidazole obtained in Reference Example 2, 1.309 g of 1-imidazolylthioacetamide hydrochloride was obtained by the same manner as described in

The synthetic route of 98873-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5565479; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem