Acetic Anhydride → N-{5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}acetamide

HRID 1899091Notes

Reaction equation

HRID 1899091 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH2:13])=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([NH:13][C:24](=[O:26])[CH3:25])=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 104978555-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine

Product 1

HCID 23372715N-{5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine (1.2 g) and acetic anhydride (0.36 ml) in dichloromethane (12 ml) was stirred at ambient temperature for 2 hours, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (3:1) to give a brown powder of N-{5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}acetamide (0.77 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-164d08cb9ccb4c25a8010106bcb2e0ae
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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