Carbon Disulfide → 1-methyl-6-[5-[[3-(trifluoromethyl)benzyl]thio]-1,3,4-oxadiazol-2-yl]-1H-benzimidazole

HRID 452745Notes

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]([NH:13][NH2:14])=[O:12])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.C(N(CC)CC)C.[C:22](=S)=[S:23].[OH-].[K+].[F:27][C:28]([F:38])([F:37])[C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Cl>C(O)C.C(OCC)(=O)C>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[O:12][C:22]([S:23][CH2:32][C:31]4[CH:34]=[CH:35][CH:36]=[C:29]([C:28]([F:38])([F:37])[F:27])[CH:30]=4)=[N:14][N:13]=3)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution (5 mL) of 1-methyl-1H-benzimidazole-6-carbohydrazide (0.20 g, 1.05 mmol), triethylamine (0.18 mL, 1.26 mmol) and carbon disulfide (0.16 mL, 2.63 mmol) in ethanol was heated under reflux overnight. The reaction mixture was cooled to 0° C., potassium hydroxide (58.9 mg, 1.05 mmol) and 3-(trifluoromethyl)benzyl chloride were added, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to give the title compound (49.9 mg, yield 12%) as colorless crystals.

Workup

temperatureunder reflux overnight
washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record: ord-05670623a6d44dc7ac21f34a284f126f
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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