Acetic Anhydride → 3-Chloroacetanilide

HRID 1087126Notes

Reaction equation

HRID 1087126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9](OC(=O)C)(=[O:11])[CH3:10]>>[C:9]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=1)(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 79323-Chloroaniline

Product 1

HCID 114933-ChloroacetanilideYield 226.8%

Conditions

Temperature
90 °C

Procedure

To 3-chloroaniline (10 g, 0.078 mol) was added portionwise acetic anhydride (32 g, 0.314 mol) in such a manner as to keep the temperature of the reaction mixture below 85° C. The reaction mixture was then stirred at 90° C. for 4 hours and then cooled to room temperature. The reaction mixture was then poured carefully into ice water, extracted with ethyl acetate and dried over sodium sulfate. The solvent was removed, yielding 30 g of N-acetyl-3-chloroaniline.

Workup

  1. customthe temperature of the reaction mixture below 85° C
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-c22f2be1bb7d4cd7a687f81dea07ae3a
Source dataset
uspto-grants-1991_07
Patent number
US05034410

Reaction notes

Loading…