Chloroacetyl chloride → 2-Chloro-N-(2-chloro-4-fluoro-6-methylphenyl)-N-(4-methylphenyl)acetamide

HRID 603342Notes

Reaction equation

HRID 603342 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]([C:20](=[O:21])[CH2:19][Cl:18])[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 579521662-Chloro-4-fluoro-6-methyl-N-(4-methylphenyl)benzenamine

Product 1

HCID 579521562-Chloro-N-(2-chloro-4-fluoro-6-methylphenyl)-N-(4-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.32 g of N-(2′-Chloro-4′-fluoro-6′-methylphenyl)-4-methylaniline is reacted with chloracetylchloride (1.76 g) at 90° C. for 30 minutes. The cooled mixture is stirred with toluene (20 ml) and aqu. sodium carbonate for 30 minutes and the organic phase is evaporated. The residue is purified flash-chromatography on silica using toluene affording 1.04 g of N-(2′-chloro-4′-fluoro-6′-methylphenyl)-N-chloroacetyl-4-methylaniline as a solid which is recrystallised from heptane/2-propanol (9:1), mp.: 96-97° C.

Workup

  1. customthe organic phase is evaporated
  2. customThe residue is purified flash-chromatography on silica
  3. customis recrystallised from heptane/2-propanol (9:1), mp.: 96-97° C.

Sources & evidence

ORD record
ord-ec253b70644c48d1956d6436cc69e44a
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Reaction notes

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