Author: Jessica.F

934-22-5, 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. 934-22-5 name is 6-Aminobenzimidazole, 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.

To the solution of 1H-benzimidazol-5-amine 121 (0.68 g, 5.11 mmol) in acetic acid (20 mL), the Compound 120a (1.06 g, 5.62 mmol) was added and stirred at room temperature for 20 minutes. TMSCN (1 mL) was added dropwise to the reaction mixture and continuously stirred for 2 hours. After reaction completing, the reaction mixture was concentrated under reduced pressure to yield a viscous liquid. The viscous liquid was diluted with ethyl acetate (10 mL) and water. The diluted solution was adjusted to the pH 6-7 with ammonia at an ice-bath. The neutralized solution was extracted with ethyl acetate (20 mL x 4), dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a viscous dark-yellow solid. The solid was dissolved in ethyl acetate (15 mL) and brine (15 mL). The mixture was stirred at room temperature for 2 minutes to form the pale-yellow precipitates. The pale-yellow precipitates was filtered and washed with water. The filtrate was dried over sodium sulfate and concentrated under reduced pressure to obtain the pale- yellow solid. Those pale-yellow solids were combined as the desired product 122a at a yield of 96%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Patent; SHIH, Chuan; NATIONAL HEALTH RESEARCH INSTITUTES; ACADEMIA SINICA; CHEN, Chih-Hao; CHEN, Chiung-Tong; WANG, Hwei-Jiung; HUANG, Kai-Fa; (130 pag.)WO2020/47360; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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. 641571-11-1.

Example 15; Preparation of Nilotinib.3HCl (crude)3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylbenzoyl chloride dihydrochloride of formula (X-Cl).2HCl (105 gms) was added to dichloromethane (1000 ml) and 3-(trifluoromethyl)-5-(4-methyl-1H-imidazol-1-yl)benzenamine of formula I (71 gms) at 25-40 C. The temperature was raised to reflux point and was stirred at this temperature for 10-12 Hours. The reaction mixture was then cooled to 30-20 C. The obtained slurry was filtered and the solid was washed with dichloromethane (200 ml). The wet product was dried at 40-60 C. under reduced pressure.The X-ray powder diffraction of the obtained product is shown in FIG. 3. The X-ray powder diffraction of the obtained product after exposure to 100% humidity for 96% is shown in FIG. 4. Yield: 90-92% Purity: 85-90% Hydrochloride content (by Argentometry titration): 16.8%.

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

7189-69-7, 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. 7189-69-7 name is 1,1′-Sulfonyldiimidazole, 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: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Sulfonyldiimidazole, and friends who are interested can also refer to it.

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

288-32-4, Name is 1H-Imidazole, 288-32-4, 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.

In a 50 mL round-bottomed flask, imidazole (1 mmol), phenylboronicacid (1.2 mmol), K2CO3 (1.5 mmol), nanocatalyst (15mol% with respect to imidazole substrate) were added andstirred in MeOH-H2O (1:1) under air at r.t. for the requiredtime, monitoring by TLC. After completion, the mixture wasdiluted with H2O and the product was extracted with EtOAc(3¡Á). The combined extracts were washed with brine (3¡Á) anddried over Na2SO4. The product was purified using columnchromatography (60-120 mesh silica gel, eluting with EtOAc-hexane). The product was isolated as white solid. 1H NMR (400MHz, CDCl3): delta = 7.87 (s, 1 H), 7.50-7.47 (m, 2 H), 7.40-7.35 (m,3 H), 2.28 (m, 1 H), 7.21 (s, 1 H) ppm. 13C NMR (100 MHz,CDCl3): delta = 137.4, 135.6, 130.3, 129.9, 127.6, 121.6, 118.3 ppm.

Statistics shows that 1H-Imidazole is playing an increasingly important role. we look forward to future research findings about 288-32-4.

Reference:
Article; Borah, Raju Kumar; Raul, Prasanta Kumar; Mahanta, Abhijit; Shchukarev, Andrey; Mikkola, Jyri-Pekka; Thakur, Ashim Jyoti; Synlett; vol. 28; 10; (2017); p. 1177 – 1182;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, 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 39021-62-0 as follows.

A mixture of (E)-4-(benzylideneamino) isobenzofuran-1(3H)-one (474 mg, 2 mmol) and 1-methyl-1H-imidazole-5-carbaldehyde (220 mg, 2 mmol) in ethyl propionate (20 mL) was cooled to 0 C. Then a solution of sodium ethoxide in ethanol [sodium (184 mg, 8 mmol) in ethanol (10 mL)] was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL¡Á4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1 to 3:7) to give ethyl 3-(1-methyl-1H-imidazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (170 mg, yield 23%). LC-MS (ESI) m/z: 376 (M+1)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39021-62-0, and friends who are interested can also refer to it.

Reference:
Patent; LEAD THERAPEUTICS, INC.; US2010/35883; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10364-94-0, Name is (1H-Imidazol-1-yl)(phenyl)methanone, 10364-94-0, 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.

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) and 0.15 mL DMF (dry) was added DBU(0.2 equiv.), and the mixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in 0.5 mL MeCN (dry) was added to the reaction mixture in two portions and it was allowed to stir at 50C for 8 h. MeCN was removed under reduced pressure and the resulting mixture was purified by flashcolumn chromatography (ethyl acetate/petroleum ether = 1:1 to 10:1) to afford benzoylated products.

Statistics shows that (1H-Imidazol-1-yl)(phenyl)methanone is playing an increasingly important role. we look forward to future research findings about 10364-94-0.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3097-21-0, 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. 3097-21-0 name is 1,3-Dimethyl-1H-benzo[d]imidazol-2(3H)-one, 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.

Take 1,3-dimethyl-1,3-dihydro-2H-benzo [d] imidazol-2-one (1.0 g, 6.1 mmol),Add to chlorosulfonic acid and react at room temperature for 5 hours;After the reaction is completed, water is added to precipitate a solid, which is filtered with suction, recrystallized, and filtered with suction, and the filter cake is dried under infrared.A gray solid was obtained with a yield of 88%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dimethyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; China Pharmaceutical University; Sun Haopeng; Mo Jun; Li Qihang; Yang Hongyu; Chen Yao; Chen Tingkai; Li Qi; Guo Yan; Liu Zongliang; Feng Feng; Liu Wenyuan; (19 pag.)CN110776494; (2020); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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. 4857-06-1

2-Chloro-5-nitrobenzimidazole (19) To 210 mL of fuming HNO3, 2-chlorobenzimidazole (13.42 g, 87.95 mmole) was added portionwise over a period of 10 min with stirring and ice-H2 O cooling. After the addition, the cooling bath was removed and stirring was continued at room temperature overnight. This reaction mixture was cooled to ~0 C., poured into 300 mL of ice, and neutralized carefully with conc. NH4 OH to ~pH 8. The resulting suspension was filtered. The yellowish solid product was washed with portions of H2 O and air-dried. The filtrate and washings were combined and extracted with EtOAc (200 mL*2). The EtOAc solution was washed with sat. NaCl solution (200 mL*2), dried (Na2 SO4), and evaporated to give 1.3 g of a yellowish solid. The solid was combined with the major part of the product and was recrystallized from MeOH to give 16.34 g (5 crops, 94%) of 19 as yellowish crystals. mp 235-237

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4857-06-1, its application will become more common.

Reference:
Patent; The Regents of the University of Michigan; US5360795; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 7189-69-7 name is 1,1′-Sulfonyldiimidazole, 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. 7189-69-7

To a solution of compound Int-TG1-3 (530 mg, 1.2 mmol) in dry THF (25 ml) was added 1,1 ?-Sulfonyldiimidazole (477 mg, 2.4 mmol) and C52CO3 (196mg, 0.6 mmol). After 18hours under reflux, the mixture was quenched with 2 N aq. HC1 (100 mL). The organic layer was extracted with EtOAc (2 x 20 mL), dried over anhydrous Mg504, filtered and concentrated. The residue was purified by column chromatography to produce the compound Int-TG12 (396 mg, 58%).?H-NIVIR (400 MHz, CDC13) 5 7.84 (s, 1H), 7.35 (s, 1H), 7.34-7.3 1 (m, 1H), 7.20-7.16(m, 2H), 7.05 (t, 1H), 6.86 (m, 1H), 5.51-5.45 (m, 2H), 5.10 (dd, J = 3.6 Hz, 1H), 4.98 (d, J = 8Hz, 1H), 2.24 (s, 3H), 2.13(s, 3H), 2.07 (s, 3H), 2.04 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Sulfonyldiimidazole, and friends who are interested can also refer to it.

Reference:
Patent; INTOCELL, INC.; PARK, Taekyo; WOO, Sung Ho; KIM, Sunyoung; PARK, Suho; CHO, Jongun; JUNG, Doohwan; SEO, Donghoon; LEE, Jaeho; LEE, Sangkwang; YUN, Sanghyeon; LEE, Hyang Sook; PARK, Okku; SEO, Beomseok; (316 pag.)WO2019/8441; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1615-14-1

The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 2.72 g (9.8 mmol) of 1-tetradecyl bromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 2.70 g (73%). Mp= 40-42 C.IR-spectrum (KBr), cm-1: 3532, 3330, 3134, 3069, 2917, 2850, 1564,1472, 1379, 1165,1071, 873, 792, 720. 1H NMR spectrum, 400 MHz (CDCl3), delta, ppm, J/Hz: 0.87 t (3H, J=6.8), 1.25-1.33m (22 H),1.87-1.91m (2 H), 3.98 t (2H, J=4.9), 4.26 t (2H, J=7.5), 4.53 t (2H,J=4.9), 7.31 s (1 H), 7.63 s (1 H), 9.73 s (1 H). ESI MS, m/z: 309.5 [MBr]+.Calculated, %: C19H37 N2 OBr: C 58.60; H 9.57; N 7.19; Br 20.52;found, %: C 58.02; H 10.05; N 7.21; Br 19.99.

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, 1615-14-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem