Water → 2-((5,6-Dimethylbenzimidazole-2-ylthio)methyl)benzoic acid methyl ester

HRID 916077Notes

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.[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29]Br.O>CN(C)C=O>[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][S:9][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([CH3:1])[C:11]([CH3:12])=[CH:10][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the resulting 5,6-dimethylbenzimidazole-2-thiol (89 mg, 0.50 mmol) in dimethylformamide (2 ml), triethylamine (84 μl, 0.6 mmol) and 2-bromomethyl benzoic acid methyl ester (137 mg, 0.6 mmol) were added. After the resulting solution was stirred at 80° C. for 1.5 hours, water was added, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous magnesium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the title compound (146 mg, yield 90%). The compound was confirmed by identification of molecular weight using LC-MS. Calculated M=326.11, measured (M+H)+=327.2

Workup

extractionfollowed by extraction with ethyl acetate
dry with materialAfter drying the ethyl acetate phase with anhydrous magnesium sulfate, it
concentrationwas concentrated
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-793390cb5ac94ca9b2dab1ef29ba11d3
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268145B2

Reaction notes

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