2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole synthesis
- Product Name:2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole
- CAS Number:103577-40-8
- Molecular formula:C16H14F3N3OS
- Molecular Weight:353.36
128430-66-0
134469-07-1
103577-40-8
2-Chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (91 g, 0.38 mol) and 1H-benzo[d]imidazole-2-thiol (57 g, 0.38 mol) were used as raw materials, suspended in methanol (1 L), and benzyltributylammonium bromide (2.15 g) was added as a phase transfer catalyst. A 30% NaOH solution (65 mL) was added slowly and dropwise over a period of 1 h, followed by stirring the reaction for 2 h at room temperature. Upon completion of the reaction, water (300 mL) was added to the reaction mixture and stirring was continued for 30 min. The mixture was cooled to 10 °C and the pH was adjusted to 9 with 35% HCl, at which point the target product 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole precipitated as a precipitate. The precipitate was collected by filtration and washed sequentially with 50% methanol and water. Finally, the product was dried under vacuum at 50 °C to give 129 g in 96% yield.
128430-66-0
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134469-07-1
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103577-40-8
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Yield:103577-40-8 96%
Reaction Conditions:
with benzyl tri-n-butylammonium bromide;sodium hydroxide in methanol at 20; for 3 h;Reagent/catalyst;
Steps:
1.2 (2) Preparation of 2 - [[2- (3-methyl-4- (2,2,2-trifluoroethoxy) pyridyl) methyl] -thio] -1H-benzimidazole
2-chloromethyl-3-methyl-4- (2,2,2-trifluoroethoxy) pyridine (91 g, 0.38 mol)2-mercaptobenzimidazole (57 g, 0.38 mol),Suspended in methanol (1 L)Benzyltributylammonium bromide (2.15 g, 0.006 mol)A 30% NaOH solution (65 mL) was added dropwise over 1 hour,Room temperature reaction 2h.To the mixture was added 300 mL of water,Stir for 30 minutes.10 ° C with 35% HCl adjusted to pH 9,Precipitation precipitation.filter,Followed by washing with 50% methanol and water.Dried at 50 ° C under vacuum,To give 2 - [[2- (3-methyl-4- (2,2,2-trifluoroethoxy) pyridin-yl) methyl] - thio] -1H- benzimidazole-129g,Yield 96%.
References:
Shijiazhuang Du Zhi Pharmaceutical Technology Co., Ltd.;Fang Yu;Du Yumin CN106543146, 2017, A Location in patent:Paragraph 0025; 0031; 0032; 0041; 0045; 0049; 0053-0069
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103577-40-8
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103577-40-8
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103577-66-8
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103577-40-8
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37699-43-7
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103577-40-8
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$7.00/250mg