Acetic Anhydride → 7-(3-Acetamidophenyl)-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644524Notes

Reaction equation

HRID 644524 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=[N:16][C:12]=3[CH:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[C:33]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=[N:16][C:12]=3[CH:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 114623287-(3-Aminophenyl)-1-phenyl-5-trifluoromethylbenzimidazole

Product 1

HCID 114067807-(3-Acetamidophenyl)-1-phenyl-5-trifluoromethylbenzimidazoleYield 76%

Procedure

A solution of 7-(3-aminophenyl)-1-phenyl-5-trifluoromethylbenzimidazole (0.32 g, 0.9 mmol) in acetic anhydride (3 ml) was stirred at ambient temperature for one hour. Saturated, aqueous sodium carbonate was added and the resultant mixture was extracted with ethyl acetate. This organic extract was washed with water and brine, successively, dried over magnesium sulphate, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (97:3, v/v) to afford the desired product (0.27 g, 76%) m/z, 396.1 (M+H)+.

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. extractionThis organic extract
  3. washwas washed with water and brine
  4. dry with materialsuccessively, dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography on silica gel eluting with a mixture of dichloromethane and methanol (97:3

Sources & evidence

ORD record
ord-af3390c0222441b49308ca979008ec6f
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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