Dimethylformamide → 2-(2-ethylsulfanyl-phenyl)-1-methyl-6-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole

HRID 923781Notes

Reaction equation

HRID 923781 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([C:19]([F:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])=[CH:18][C:12]=2[N:11]=1)[CH3:2].[CH3:29]N(C=O)C.[H-].[Na+].IC>O>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]([CH3:29])[C:12]2[CH:18]=[C:17]([C:19]([F:28])([C:20]([F:21])([F:22])[F:23])[C:24]([F:27])([F:25])[F:26])[CH:16]=[CH:15][C:13]=2[N:14]=1)[CH3:2].[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:14]([CH3:29])[C:13]2[CH:15]=[CH:16][C:17]([C:19]([F:28])([C:20]([F:21])([F:22])[F:23])[C:24]([F:27])([F:25])[F:26])=[CH:18][C:12]=2[N:11]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178477270HCID 178477270, compound

Product 2

HCID 867082252-(2-ethylsulfanyl-phenyl)-1-methyl-6-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazoleHCID 867082262-(2-ethylsulfanyl-phenyl)-1-methyl-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(2-ethylsulfanyl-phenyl)-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (97 mg) and DMF (10 mL), sodium hydride (11 mg) and iodomethane (16 μL) were added under ice-cooling. The mixture was heated to room temperature, and stirred for 5 hours. The reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 35 mg of 2-(2-ethylsulfanyl-phenyl)-1-methyl-6-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (hereinafter, Present Compound 304) and 80 mg of 2-(2-ethylsulfanyl-phenyl)-1-methyl-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (hereinafter, Present Compound 305).

Workup

  1. additionwere added under ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f245d03f182d45f6907935371b89d51e
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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