Acetic Anhydride → n-(2,5-difluorophenyl)acetamide

HRID 2248260Notes

Reaction equation

HRID 2248260 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1C=CC=CC=1>[CH3:11][C:10]([NH:4][C:3]1[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:2]=1[F:1])=[O:12]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 677752,5-Difluoroaniline

Product 1

HCID 242830n-(2,5-difluorophenyl)acetamideYield 94.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20.5 g of 2,5-difluoroaniline was dissolved in 68 ml of benzene, and 17.8 g of acetic anhydride was dropwise added. Fifteen hours later, benzene was distilled off, and the residue was washed with ethyl ether to obtain 25.6 g of 2,5-difluoroacetanilide as white crystals. Then, this compound was dissolved in 98% sulfuric acid, and 60% nitric acid was dropwise added at a temperature of not higher than 0° C. After the dropwise addition, the mixture was stirred for three hours at room temperature, and poured on ice. Precipitated crystals were collected by filtration and dried to obtain 25.9 g of the above-identified compound as yellow crystals.

Workup

  1. distillationFifteen hours later, benzene was distilled off
  2. washthe residue was washed with ethyl ether

Sources & evidence

ORD record
ord-211ebb41bcad4b99b1f3d0063dcdc009
Source dataset
uspto-grants-1991_08
Patent number
US05039331

Reaction notes

Loading…