Water → 2-((5,6-Dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile

HRID 916089Notes

Reaction equation

[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.Br[CH2:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[C:24]#[N:25].O>CN(C)C=O>[CH3:12][C:11]1[C:2]([CH3:1])=[CH:3][C:4]2[N:8]=[C:7]([S:9][CH2:21][C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[C:24]#[N:25])[NH:6][C:5]=2[CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 5,6-dimethylbenzimidazole-2-thiol (713 mg, 4 mmol) in dimethylformamide (10 ml), triethylamine (836 μl, 6 mmol) and 2-bromomethylbenzonitrile (1176 mg, 6 mmol) were added. After stirring at 80° C. overnight, water was added to the mixture, followed by extraction with ethyl acetate. After the ethyl acetate phase was dried with anhydrous sodium sulfate, it was concentrated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to obtain 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile (1159 mg, yield 99%).

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialAfter the ethyl acetate phase was dried with anhydrous sodium sulfate, it
concentrationwas concentrated
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record: ord-479d004c354b43629cc0fc3b79238409
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268145B2

Reaction notes

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