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

HRID 916079Notes

Reaction equation

C(N(CC)CC)C.[C:8]([O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20]CBr)([CH3:11])([CH3:10])[CH3:9].[CH3:24][C:25]1[C:34]([CH3:35])=[CH:33][C:28]2[N:29]=[C:30]([SH:32])[NH:31][C:27]=2[CH:26]=1.O>CN(C)C=O>[C:8]([O:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][S:32][C:30]1[NH:31][C:27]2[CH:26]=[C:25]([CH3:24])[C:34]([CH3:35])=[CH:33][C:28]=2[N:29]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Triethylamine (276 μl, 1.98 mmol) and 2-(bromoethyl)benzoic acid t-butyl ester (538 mg, 1.99 mmol) were added to 5,6-dimethylbenzimidazole-2-thiol (236 mg, 1.32 mmol) in 2 ml of dimethylformamide, which was then stirred at 80° C. for 3 hours. After the reaction was complete, water was added, followed by extraction with ethyl acetate. After drying the ethyl acetate phase with anhydrous sodium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzoic acid t-butyl ester (288 mg, yield 59%).

Workup

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

Sources & evidence

ORD record: ord-1e8aa961a1544995af0c9ff8ffb924b2
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268145B2

Reaction notes

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