Aniline → Butanamide, 4-chloro-3-oxo-N-phenyl-

HRID 434559

Reaction equation

HRID 434559 reaction equation
Cl[C:2]1([CH2:7][Cl:8])[O:5][C:4](=[O:6])[CH2:3]1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:8][CH2:7][C:2](=[O:5])[CH2:3][C:4]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6]

Participants

5

Reactant 2

HCID 6115AnilineHCID 137182814-Chloro-4-(chloromethyl)oxetan-2-one

Product 1

HCID 38215Butanamide, 4-chloro-3-oxo-N-phenyl-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

7.8 Parts of 4-chloro-4-chloromethyloxetan-2-one are dissolved in 150 parts of methylenechloride containing 4.2 parts of anhydrous sodium bicarbonate and the solution is cooled to 0° C. 4.7 Parts of aniline are then added over 30 minutes and the reaction mixture is finally stirred for 48 hours at room temperature. The solids are then filtered off and the filtrate evaporated. The residue is crystallised twice from chloroform to give γ-chloroacetoacetanilide, m.p. 142°-143° C.

Workup

  1. filtrationThe solids are then filtered off
  2. customthe filtrate evaporated
  3. customThe residue is crystallised twice from chloroform

Sources & evidence

ORD record
ord-1de118cf597a444a877d081882727599
Source dataset
uspto-grants-1983_08
Patent number
US04398033

Linked notes

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