Methyl iodide → 7-(3-(N-Methyl acetamido)phenyl)-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644529Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[C:16]3[N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[N:19][C:15]=3[CH:14]=[C:13]([C:26]([F:29])([F:28])[F:27])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[H-].[Na+].I[CH3:33]>O1CCCC1>[CH3:33][N:4]([C:5]1[CH:6]=[C:7]([C:11]2[C:16]3[N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[N:19][C:15]=3[CH:14]=[C:13]([C:26]([F:29])([F:28])[F:27])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[C:1](=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 7-(3-acetamidophenyl)-1-phenyl-5-trifluoromethylbenzimidazole (0.35 g, 0.88 mmol) in anhydrous tetrahydrofurane (5 ml) was added sodium hydride (0.09 g 60% dispersion in mineral oil, 2.2 mmol). The resultant mixture was stirred for one hour at ambient temperature, whereafter iodomethane (0.44 ml, 7 mmol) was added and the temperature was raised to 40° C. for 30 min. The cooled mixture was partitioned between water and ethyl acetate. The organic layer was washed with water, dried over magnesium sulphate and concentrated under reduced pressure. The concentrate was eluted through silica gel with a mixture of dichloromethane and methanol (97:3, v/v). Removal of solvent from the eluate afforded the title product (0.13 g, 36%) m/z, 410.1 (M+H)+.

Workup

additionwas added
customThe cooled mixture was partitioned between water and ethyl acetate
washThe organic layer was washed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure
washThe concentrate was eluted through silica gel with a mixture of dichloromethane and methanol (97:3
customRemoval of solvent from the

Sources & evidence

ORD record: ord-abe6bfd9dda34a948866b10a6d7e9a42
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700638B2

Reaction notes

Loading…