Water → 2-(2,4-dichlorophenyl)-N-phenylacetamide

HRID 1721917Notes

Reaction equation

HRID 1721917 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.O>CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 8471TriethylamineHCID 2758147(2,4-Dichlorophenyl)acetyl chloride

Product 1

HCID 27048312-(2,4-dichlorophenyl)-N-phenylacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,4-Dichlorophenylacetyl chloride (0.075 mol) was added dropwise over 1 h to a stirred solution of aniline (6.8 g) and triethylamine (7.6 g) in dry ether (200 ml) at 0°-5° C. The reaction mixture was allowed to warm up to room temperature overnight. It was then poured into iced water. An oily layer separated out and gradually solidified. This was recrystallised from diisopropyl ether to give 2-(2,4-dichlorophenyl)acetanilide, m.p. 145.6°-146.5° C.

Workup

  1. customAn oily layer separated out
  2. customThis was recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-197bf963d1454b89a71d48999e46eba3
Source dataset
uspto-grants-1989_08
Patent number
US04853400

Reaction notes

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