Tetrahydrofuran → 2-((1-((2,5-Dimethylphenyl)methyl)-5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile

HRID 916090Notes

Reaction equation

[H-].[Na+].O1[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:8][C:9]1[C:27]([CH3:28])=[CH:26][C:12]2[N:13]=[C:14]([S:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])[NH:15][C:11]=2[CH:10]=1.Cl[C:30]1[CH:37]=CC(Cl)=[CH:34][C:31]=1[CH2:32]Cl>O>[CH3:4][C:5]1[CH:37]=[CH:30][C:31]([CH3:34])=[CH:32][C:6]=1[CH2:7][N:15]1[C:11]2[CH:10]=[C:9]([CH3:8])[C:27]([CH3:28])=[CH:26][C:12]=2[N:13]=[C:14]1[S:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]#[N:25]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (178 mg, 4.90 mmol) and tetrahydrofuran (30 ml) were added to a previously dried reaction vessel. To the mixture were added 2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile (719 mg, 2.45 mmol) and 2,5-dichlorobenzyl chloride (543 μl, 4.90 mmol), and the mixture was stirred at 60° C. for 40 minutes. Water was added thereto, 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=3:1) to obtain 2-((1-((2,5-dimethylphenyl)methyl)-5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile (370 mg, yield 37%).

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=3:1)

Sources & evidence

ORD record: ord-2c64f644d0a140b499da6f8248d16245
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268145B2

Reaction notes

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