Benzimidazole → 1-(4'-Phenylsulfonylphenyl)benzimidazole

HRID 391612

Reaction equation

[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].[C:12]1([S:18]([C:21]2[CH:26]=[CH:25][C:24](Cl)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[C:12]1([S:18]([C:21]2[CH:26]=[CH:25][C:24]([N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of benzimidazole (11.8 g, 0.10 mol) in DMF (500 ml), is added, at room temperature under nitrogen, sodium hydride (60% in mineral oil, 4.4 g, 0.11 mol), and the mixture is stirred for 10 min. The mixture is admixed with 4-chlorophenyl phenyl sulfone (26.1 g, 0.10 mol) and stirred at 100° C. for 16 h. After again adding sodium hydride (60% in mineral oil, 2.0 g, 0.05 mol) at room temperature, the mixture is stirred at 130° C. for 16 h. After cooling to room temperature, the mixture is added to ice-water. Precipitated product is filtered off and washed with water. Yield: 91%.

Workup

temperatureAfter cooling to room temperature
filtrationPrecipitated product is filtered off
washwashed with water

Sources & evidence

ORD record: ord-103c94644465470c94337645ee1c5580
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08384068B2

Linked notes

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