Author: Jessica.F

Related Products of 615-16-7, These common heterocyclic compound, 615-16-7, name is 2-Hydroxybenzimidazole, 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 a stirred solution of compound 114 (1 g, 7.46 mmol) in CH2C12 (10 mL) under argon atmosphere was added chlorosulfonic acid (1 mL, 14.92 mmol) at 0 C; heated to reflux and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo and the residue diluted with water (10 mL); neutralized with aqueous NaOH solution and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford compound 115 (980 mg, 58%) as an off-white solid. TLC: 10% MeOH/ CH2C12 (Rf. 0.5); 1H-NMR (DMSO-i/tf, 400 MHz): delta 10.66 (s, 1H), 10.61 (s, 1H), 7.24 (d, J= 6.4 Hz, 1H), 7.18 (s, 1H), 6.85 (d, J = 8.4 Hz, 1H).

The synthetic route of 615-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ARNOLD, Lee Daniel; MAAG, Hans; TURNER, JR., William W.; (274 pag.)WO2016/168619; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 28890-99-5, These common heterocyclic compound, 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, 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.

[28890-99-5] (3.0 g, 14.4 mmol) is dissolved in THF (0204) (100 ml) and the suspension is cooled to 0 C. NaH as 60% suspension (691 mg, 17.3 mmol) is added in portions. [98-59-9] is dissolved in THF (50 ml) and the solution is dropped into the reaction mixture. It is stirred over night at room temperature. Saturated NH4CI solution (150 ml) is slowly added. It is extracted with ethyl acetate. The crude product is used without further purification.

The synthetic route of 28890-99-5 has been constantly updated, and we look forward to future research findings.

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

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 16681-56-4 as follows. Computed Properties of C3H3BrN2

Obtained in Example 50 (a) (S) -1-tert- butoxycarbonylamino-4- (5-chloro-7- (4,4,5,5-dioxa -1,3,2- borane-2-yl)benzoxazol-2-yl) -3-methyl piperazine (48 mg, 0.1mmol), 2- bromo -1H- imidazole (29 mg, 2.0 eq.), Tetrakis(triphenylphosphine) palladium (0) (11.6 mg, 0.1 eq), potassium carbonate (55 mg, 4.0 equiv) 1, 4-dioxane (800muL) and water (200muL) for dissolution, and under an argon atmosphere in an oil bath from 110 4 hours with stirring did. Water was added to the reaction mixture, the product extracted with ethyl acetate, an organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by preparative TLC (developing solvent, methanol: chloroform = 1: 19) to give the title compound 21.3 mg.

According to the analysis of related databases, 16681-56-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MeijiSeika Pharma Corporation; Kikuchi, Jika; Tabata, Yuji; Yamakawa, Takeru; Matsuhira, Takashi; Watanabe, Naoko; Kuboda, Natsuki; Kaneda, Kaoru; (143 pag.)KR2016/30503; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3314-30-5, 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 3314-30-5 as follows.

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0°C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3- thiazole-4-carboxamide dihydrochloride (192) (143 mg, 0.37 mmol), 1 H-1 ,3-benzodiazole-2-carbaldehyde (70.1 mg, 0.48 mmol), MgS04 (200 mg) in MeOH (10 ml) at room temperature for 3 d, followed by addition of NaBH4 (28 mg, 0.74 mmol) gave the title compound (94 mg, 56percent) as a white solid after purification by prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.19 (s, 1 H), 8.71 (t, J = 5.6 Hz, 1 H), 8.37 (dt, J = 4.6, 1.3 Hz, 1 H), 7.70 (ddd, J = 10.0, 8.4, 1.1 Hz, 1 H), 7.54 (d, J = 7.2 Hz, 1 H), 7.45 (d, J = 7.0 Hz, 1 H), 7.40 (dt, J = 8.6, 4.4 Hz, 1 H), 7.14 (t, J = 7.5 Hz, 2H), 4.66 – 4.58 (m, 2H), 3.97 (s, 2H), 3.12 (t, J = 6.3 Hz, 2H), 2.94 (t, J = 6.3 Hz, 2H) HPLCMS (Method A): [m/z]: 445.1 [M+H]+

According to the analysis of related databases, 3314-30-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4278-08-4,Some common heterocyclic compound, 4278-08-4, name is 2-(4-Fluorophenyl)-1H-imidazole, molecular formula is C9H7FN2, 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.

Into a 15mL pressure tube, sequentially add 1e (48.6 mg, 0.3 mmol), dichloromethane (3 mL), 2a (84.7 mg, 0.45 mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7 mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3e (57.5 mg, 55%) as a white solid.

The synthetic route of 4278-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Henan Normal University; Zhang Xinying; Zhang Linghua; Xu Yuanshuang; Fan Xuesen; (23 pag.)CN110372708; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 934-32-7, 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. 934-32-7 name is 1H-Benzo[d]imidazol-2-amine, 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 mixture of 2-aminobenzimidazole (1 mmol), malononitrile (1 mmol) and 4-fluorobenzaldehyde (1 mmol) in ethylene glycol (5 mL), SSA (42.6 mg, 0.11 mol %) wasadded. The mixture was heated at 50 C for 5 minutes. After completion of the reaction(TLC), 10 mL EtOAc was added to the reaction mixture and the catalyst was recovered by filtration. The organic layer was dried over Na2SO4; the solvent was evaporated and purified by recrystallization from ethanol to give compounds 1b. Yield 87%

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

Reference:
Article; Basyouni, Wahid M.; Abbas, Samir Y.; Abdelazeem, Nagwa M.; El-Bayouki, Khairy A. M.; El-Kady, Mohamed Y.; Synthetic Communications; vol. 49; 22; (2019); p. 3112 – 3120;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 934-32-7, These common heterocyclic compound, 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, 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 the requested benzylic aldehyde (1 mmol),2-aminobenzimidazole or 3-amino-1,2,4-triazole (1 mmol),beta-diketone (1 mmol) and NS-C4(DABCO-SO3H)2·4Cl(20 mg, 10 mol %) was heated at 90 C under solvent-freeconditions. The progress of the reaction was monitoredby TLC (n-hexane: EtOAc, 70:30). After completion ofthe reaction, the reaction mixture was cooled to roomtemperature and 3 mL of water was added to it. Thecatalyst was dissolved in water and filtered for separation ofthe crude product. The separated product was washed twicewith water (2 × 5 mL), and the crude product was purifiedby recrystallization in ethanol.

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Journal of the Iranian Chemical Society; vol. 14; 11; (2017); p. 2275 – 2286;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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. SDS of cas: 32673-41-9

A mixture of 1,2,3,4-tetrahydro-quinoline (Intermediate F1) (Commercially available from Aldrich) (1.62 mL, 12.6 mmol) and 4-hydroxymethyl-imidazole hydrochloride salt (commercially available from Aldrich) (Intermediate F2) (0.70 g, 5.1 mmol) and sodium carbonate (1.6 g, 15.1 mmol) in water (20 mL) and dioxane (10 mL) were heated at reflux for 24 h. The mixture was cooled to rt and extracted with ethyl acetate. The organic solution was dried over MgSO4, filtered and freed of solvent. The resultant oil was purified by chromatography on silica gel with 5% NH3-MeOH: dichloromethane to give 1-(1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3) as a solid, 0.54 g (50%). 1-(1H-Imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (Intermediate F3)was subjected to the appropriate process steps in Method A to produce 4-(3,4-dihydro-2H-quinolin-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 11). 1H NMR (300 MHz, DMSO-d6): delta12.0 (s, 1H), 11.8 (s, 1H), 6.93 (t, J=6.9 Hz, 1H), 6.87 (d, J=7.2 Hz, 1H), 6.66-6.63 (m, 1H), 6.63 (s, 1H), 6.50 (t, J=6.9 Hz, 1H), 4.18 (s, 2H), 3.28 (t, J=6.3 Hz, 2H), 2.67 (t, J=6.3 Hz, 2H), 1.90-1.84 (m, 2H).

The synthetic route of 4-Imidazolemethanol hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2006/69143; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 827320-59-2, name is 1-butylsulfonic-3-methylimidazolium hydrogensulfate, 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 827320-59-2, Recommanded Product: 827320-59-2

Weigh the compound obtained in the second step1-sulfobutyl-3-methylimidazole bisulfate ionic liquid (5.06 g, 16.0 mmol)Placed in the reactor;The aqueous hydroxylamine solution 2 obtained in the first step was measured2.9 ml (32.0 mmol as hydroxylamine)Slowly added dropwise to the above ionic liquid,Low temperature (? 0 ) stirring 2h,A colorless transparent reaction liquid;The reaction solution was subjected to rotary evaporation at 70 C,A white solid product was obtained1-sulfobutyl-3-methylimidazole bisulfate ionic liquid-type hydroxylamine salt,The ionic liquid-type hydroxylamine salt was weighed and dried to weigh 4.25 g,The yield was 69.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-butylsulfonic-3-methylimidazolium hydrogensulfate, and friends who are interested can also refer to it.

Reference:
Patent; Hebei University of Technology; Wang, Yanji; Li, Zhihui; Qi, Xudong; Zhang, Dongsheng; Xu, Yuanyuan; Yang, Quisheng; Zhao, Xinqiang; (7 pag.)CN104086487; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, Computed Properties of C19H13BrN2

(4-7) Synthesis of Compound (4); Into a 300 ml three-necked flask, 1.1 g (2.1 mmole) of Intermediate 14, 1.6 g (4.6 mmole) of 2-(4-bromophenyl)-1-phenylbenzimidazole, 0.10 g (0.09 mmole) of tetrakis(triphenylphosphine)palladium(0), 20 ml of 1,2-dimethoxyethane and 6.5 ml (13 mmole) of a 2 M aqueous solution of sodium carbonate were placed under the stream of argon, and the resultant mixture was heated under the refluxing condition for 8 hours. When the reaction was completed, the organic layer was washed with water and dried with magnesium sulfate, and the solvent was removed by distillation using a rotary evaporator. The obtained crude crystals were washed with 50 ml of toluene and 100 ml of methanol, and 1.6 g of a light yellow powder substance was obtained. The obtained substance was identified to be Compound (4) by the measurement of the field desorption mass spectrum (FD-MS) (the yield: 78percent).

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, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; US8058450; (2011); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem