Tag: M.W=200-300

These common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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. Product Details of 14741-71-0

Method A 4-Amino-3-benzimidazol-2-yl-6-(4-methylpiperazinyl)hydroquinolin-2-one Ethyl 2-benzimidazol-2-ylacetate (1.1 eq) and 2-amino-5-(4-methylpiperazinyl)benzenecarbonitrile (1.0 eq) were dissolved in 1,2-dichloroethane, and then SnCl4 (11 eq) was added. The mixture was heated at reflux overnight. Upon cooling, the mixture was concentrated in vacuo. NaOH (3 M) was added to the solid, and the mixture heated at 80 C. for 0.5 hours. The solid was filtered and washed sequentially with H2O, CH2Cl2, and acetone. LC/MS indicated that the product was present in the acetone layer and the solid. These fractions were combined and purified by silica gel chromatography (5-10% MeOH in CH2Cl2 with 1% Et3N) to give the desired product. LC/MS m/z 375.4 (MH+), Rt 1.65 minutes.

The synthetic route of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chiron Coporation; US2003/28018; (2003); A1;; ; Patent; Renhowe, Paul A.; Pecchi, Sabina; Machajewski, Timothy D.; Shafer, Cynthia M.; Taylor, Clarke; McCrea JR., William R.; McBride, Christopher; Jazan, Elisa; US2002/107392; (2002); A1;,
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Related Products of 540516-28-7, 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. 540516-28-7, name is 2-(Hydroxymethyl)-5-bromobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

N-Methyl-2-methanol 5-bromobenzimidazole 50 was prepared according to the procedure by Gonzlez-Chvez et al. [28]. A solution of 5-bromo-(1H-benzimidazole-2-yl)-methanol 28 (0.60 g, 2.60 mmol), and sodium hydroxide (0.10 g, 2.60 mmol) were stirred in dry acetone (10 mL) for 30 min. Then, iodomethane (0.37 g, 2.60 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl. The solid was washed with water (100 mL) and purified by column chromatography (9:1 chloroform/ethanol) to give the desired product (50) as a bright yellow crystals Yield 16%.

The synthetic route of 2-(Hydroxymethyl)-5-bromobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
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Electric Literature of 26576-46-5, 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. 26576-46-5, name is 5-Acetoacetlamino benzimdazolone belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 13; mol of dimethyl aminoterephthalate hydrochloride is diazotized with sodium nitrite at 0 to 10 C. The clarified diazonium salt solution is added dropwise at room temperature over 1 hour to an acetate-buffered suspension of 0.1 mol of N-acetoacetyl-4-amino-1,2-benzimidazolone. As soon as coupling is at an end, the suspension is heated to 95 C. and filtered and the crude product is washed salt-free and dried. The crude pigment is suspended in a liter of 2-(2-ethoxyethoxy)ethanol and then stirred at 80 to 120 C. for three hours.The suspension is then cooled to 70 C. and filtered and the product is dried and ground. This gives 40 g of a neutrally yellow pigment having very high fastness to solvents and to overcoating.

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

Reference:
Patent; Clariant International Ltd.; US2009/198045; (2009); A1;,
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Imidazole | C3H4N2 – PubChem

Reference of 144689-93-0, 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 144689-93-0 as follows.

First, alkyl 4-(1-hydroxy-1-methylethyl)-2-propyl imidazole-5-carboxylate (20.0 g, 83.2 mmol) and sodium hydroxide powder (6.6 g, 165.0 mmol) were dissolved in 100 ml of acetone and distilled water, and the mixture was stirred and refluxed at 110 C for 3 hours. After cooling to room temperature, the acetone was removed by concentration under reduced pressure. The distilled water layer was titrated with 5N HCl acid at 0C. The solids were filtered off and dried to give compound 2 (14.46 g, 82%).

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTC Bio Co.,Ltd; Oh, Chang Hyun; Kim, Jung Hoon; Yu, Sung Won; Kim, Hyun Ir; (9 pag.)KR101628758; (2016); B1;,
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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. 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C13H10N2O

a.) 15.72 g (74.8 mmol) of 3-phenyl-1 H-benzimidazol-2-one, 6.94 g (34.0 mmol) of 1 ,3-difluoro- 4,6-dinitrobenzene and 28.87 g (136 mmol) of K3P04 were mixed together in N M P (200 mL) at 0C for 2h. The mixture was then stirred 2h at room temperature and precipitated in water fil- trated to yield 19.44 g of 2-1 as a yellow powder [Purity = 85%(H PLC)] which was used directly as it is for the next step. (0778) Mass [M+1 ] = 584.2

According to the analysis of related databases, 14813-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; FLORES, Jean-Charles; NAGASHIMA, Hideaki; (236 pag.)WO2017/93958; (2017); A1;,
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53484-15-4, name is 5-Bromo-1-methyl-1H-benzo[d]Imidazole, 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. Formula: C8H7BrN2

A mixture of 5-bromo-l-methyl-li7-benzo[7]imidazole (302.3 mg, 1.432 mmol), diphenylmethanimine (341.5 mg, 1.885 mmol), t-BuONa (271.1 mg, 2.821 mmol), BINAP (89.7 mg, 0.144 mmol) and Pd2(dba)3 (130.6 mg, 0.1426 mmol) in l,4-dioxane (10 mL) was heated to 100 C and stirred overnight under N2 atmosphere and then concentrated in vacuo. The residue was diluted with water (40 mL) and the resulting mixture was extracted with a mixed solvent of DCM/MeOH (10/1 (v/v), 50 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo to give the crude product as a brown solid (0.446 g), which was used directly in the next step without further purification.MS (ESI, pos.ion) m/z: 312.4 [M+H]+.

The synthetic route of 53484-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
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Reference of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

A solution of 4.08 g (20 mmol) compound 2 in glacial acetic acid (30 mL) wasadded dropwise to 45 % aqueous sodium nitrite solution (10 mL, 65 mmol) at0-5 8C under a nitrogen atmosphere. The reaction mixture was stirred at 20 8C for2 h then poured into ice-water and neutralized with saturated sodium carbonatesolution. The precipitate was isolated by filtration, washed with water, and vacuumdried. The solid obtained was recrystallized from methanol-diethyl ether (2:1 v/v) togive compound 3 (3.34 g; yield 72 %) as pale yellow crystals, m.p. 152.3-153.9 8C. 1H NMR (400 MHz, CDCl3) d: 1.44-1.49 (t, J = 7.2 Hz, 3H, CH3), 4.47-4.53 (q,J = 7.2 Hz, 2H, CH2), 7.26-7.69 (m, 4H, ArH), 11.06 (s, 1H, OH). IR (KBr) m(cm-1): 3416 (N-H), 3258 (O-H), 3070 (Ar-H), 1714 (C=O), 1622 (C=N), 1279,1043 (C(O)-O-C). ESI-MS m/z: calcd for C11H11N3O3 [M ? Na]? 256.2, obsd[M ? H]? 256.4.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Peizhi; Wan, Fuxian; Li, Ying; Li, Chengkun; Jiang, Lin; Research on Chemical Intermediates; vol. 41; 6; (2015); p. 3349 – 3357;,
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Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, 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.

0 ~ 5 ,A solution of 3- (4-methyl-1H-1-imidazolyl) -5-trifluoromethylaniline (24.1 g, 0.1 mol)Acetyl chloride (11.7 g, 0.15 mol) and dichloromethane (150 mL) were added to a three-necked reaction flask,Triethylamine (15.0 g, 0.15 mol) was added dropwise with stirring,After that,Heating up to 25 ~ 35 ,Reaction for 2 hours,TLC detection, to the raw material reaction completely.The reaction solution was poured into ice water, and the layers were allowed to stand. The aqueous phase was extracted with methylene chloride, the organic phase was combined, washed with 10% sodium hydrogencarbonate solution, dried, the solvent was removed under reduced pressure,Get like white solidN- [3- (4-methyl-1H-1-imidazolyl) -5-trifluoromethylbenzene] acetamide (III)(Acetyl-protected compound of formula II)

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Lixin Pharmaceutical Co., Ltd.; Xu Xuenong; Bao Zhijian; Su Jian; Xue Jia; Gu Xinyu; Huang Dongliang; Chen Wei; Wang Zhe; (6 pag.)CN107188887; (2017); A;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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 870837-18-6, Safety of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

To a solution of the thus obtained 3-methoxy-4-(4-methylimidazol-1-yl)benzaldehyde (4.00 g) in tetrahydrofuran (40 mL), diethylphosphonoacetic acid ethyl ester (4.00 mL) and lithium hydroxide monohydrate (932 mg) were added sequentially, and the reaction mixture was stirred overnight. After confirming the disappearance of the starting materials, 2N aqueous sodium hydroxide (30 mL) and ethanol (5 mL) were added to the reaction mixture, which was then stirred overnight at room temperature. The reaction mixture was cooled to 0 C., followed by addition of 2N hydrochloric acid (30 mL). The resulting precipitates were collected using a Kiriyama funnel and washed with water and ethyl acetate to give (E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid (4.61 g). The physical property data of the resulting compound are as shown below. 1H-NMR (DMSO-d6) delta (ppm): 7.81 (s,1H), 7.60 (d,J=16 Hz,1H), 7.56 (s,1H), 7.39 (d,J=8.0 Hz,1H), 7.35 (d,J=8.0 Hz,1H), 7.16 (s,IH), 6.66 (d,J=16 Hz,1H), 3.88 (s,3H), 2.15 (s,3H).

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Reference:
Patent; Eisai Co., Ltd.; US2006/241038; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 86604-86-6, These common heterocyclic compound, 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, 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.

Example 9: 3-(3,4-Dichlorophenyl)-8-[5-(trifluoromethyl)-1 H-benzimidazol-2-yl1-1 -oxa-3,8- diazaspiro[4.51decan-2-one; 2-Chloro-5-(trifluoromethyl)-1 /-/-benzimidazole (Intermediate 1 , 100 mg, 0.45 mmole) and 3-(3,4-dichlorophenyl)-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrobromide (Intermediate 16, 190.5 mg, 0.498 mmol) were dissolved in a mixture of 2-pentanol:CH3CN (4:1 , 2 ml) in a vial for microwave reactions, DIPEA was added (235.1 mul, 1.35 mmol) and the mixture was heated at 200 C for 10 minutes. The mixture was concentrated under vacuum; the crude was purified by MDAP, then the fractions were collected and purified by ion- exchange SCX to give the title compound (35.4 mg, 16%). 1 H-NMR (500MHz, CDCI3): delta 1.89-2.04 (4H, m), 3.57-3.66 (2H, m), 3.76-3.87 (2H, m), 3.95 (2H, s), 7.20-7.51 (3H, m), 7.54-7.59 (1 H, m), 7.63-7.69 (1 H, d), 7.84-7.86 (1 H, d), 11.79 (1 H, br s); MS: m/z 485 [M+H]+.

Statistics shows that 2-Chloro-6-(trifluoromethyl)benzimidazole is playing an increasingly important role. we look forward to future research findings about 86604-86-6.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem