Acetone → 2-chloro-N-(3,4-dichlorophenyl)acetamide

HRID 2285928Notes

Reaction equation

HRID 2285928 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].CC(C)=O.[Cl:14][CH2:15][C:16](Cl)=[O:17].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:14][CH2:15][C:16]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=1)=[O:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6577Chloroacetyl chlorideHCID 72573,4-DichloroanilineHCID 11430Potassium Carbonate

Product 1

HCID 2347442-chloro-N-(3,4-dichlorophenyl)acetamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

81 g (0.5 mol) of 3,4-dichloroaniline are dissolved 500 ml of acetone. 85 g (0.75 mol) of chloroacetyl chloride are poured in, over a period of 17 minutes, with stirring. The mixture is heated under reflux for 15 minutes, cooled and 350 ml of a 30% strength potassium carbonate solution in water (pH=8) are poured in. This solution is poured into a 2,000 ml Erlenmeyer flask and 500 ml of H2O+ice are added. The precipitate which appears is filtered off, washed with water, dried and recrystallised from benzene. 102 g (yield 85%) of N-chloroacetyl-3,4-dichloroaniline are thus obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. temperaturecooled
  4. additionare added
  5. filtrationThe precipitate which appears is filtered off
  6. washwashed with water
  7. customdried
  8. customrecrystallised from benzene

Sources & evidence

ORD record
ord-a0936fb58a3245ef8179e0fea953a357
Source dataset
uspto-grants-1982_04
Patent number
US04325964

Reaction notes

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