Aniline → Chloroacetanilide

HRID 1110718Notes

Reaction equation

HRID 1110718 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:15][CH2:16][C:17](Cl)=[O:18]>ClCCl>[C:2]1([NH:1][C:17](=[O:18])[CH2:16][Cl:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 6577Chloroacetyl chlorideHCID 8471Triethylamine

Product 1

HCID 11485ChloroacetanilideYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of aniline (9.3 g) and triethylamine (10.1 g) in dichloromethane (40 ml) was added dropwise during 1 hour to an ice-cooled solution of chloroacetyl chloride (11.3 g) in dichloromethane (40 ml). The mixture was further stirred for 18 hours. The organic phase was separated by filtration, washed with water (3×50 ml), dried (MgSO4) and the solvent removed by evaporation to give N-phenyl-2-chloroacetamide (6.1 g) as a white solid, mp 128°-129° C., which was used without further purification.

Workup

  1. customThe organic phase was separated by filtration
  2. washwashed with water (3×50 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-20945aab5eb44842a0c1129d5e962458
Source dataset
uspto-grants-1990_12
Patent number
US04977148

Reaction notes

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