Water → 4-Chloro-N-(2-chloro-5-methoxy-phenyl)-phenylacetamide

HRID 581049Notes

Reaction equation

HRID 581049 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1.O>C(Cl)Cl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:5][C:4]2[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:3]=2[Cl:2])=[O:28])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 906924-Chlorophenylacetyl chlorideHCID 27239002-Chloro-5-methoxyanilinium chloride

Product 1

HCID 474237744-Chloro-N-(2-chloro-5-methoxy-phenyl)-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.8 g (30 mmol) of 2-chloro-5-methoxyaniline-hydrochloride are dissolved with 7.08 g (70 mmol) of triethylamine in 100 ml methylene chloride and whilst cooling with ice 5.86 g (31 mmol) of 4-chlorophenylacetyl chloride are added dropwise. After 2 hours' stirring the mixture is added to water and extracted with methylene chloride. The extracts are dried and evaporated down. The evaporation residue is recrystallised from ether/petroleum ether. Melting point: 149-151° C.

Workup

  1. additionare added dropwise
  2. extractionextracted with methylene chloride
  3. customThe extracts are dried
  4. customevaporated down
  5. customThe evaporation residue is recrystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-4ee00fc751fb4334999374b61d58918b
Source dataset
uspto-grants-1999_07
Patent number
US05919807

Reaction notes

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