Acetic Anhydride → N-(3-Chlorophenyl)acetamide

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

Reactant 2

HCID 7918Acetic Anhydride

HCID 79323-Chloroaniline

Product 1

HCID 11493N-(3-Chlorophenyl)acetamideYield 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

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

Sources & evidence

ORD record: ord-c22f2be1bb7d4cd7a687f81dea07ae3a
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034410

Reaction notes

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