Thionyl Chloride → N-(2-fluoro-5-chlorocarbonyl-4-chlorophenyl)-2,3-dimethylmaleic acid imide

HRID 1381834Notes

Reaction equation

HRID 1381834 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9](O)=[O:10])=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]([CH3:19])[C:13]1=[O:20].CC1C(=O)NC(=O)C=1C.S(Cl)([Cl:32])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([Cl:32])=[O:10])=[CH:4][C:3]=1[N:12]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]([CH3:19])[C:13]1=[O:20]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 287932,3-DimethylmaleimideHCID 17802070N-(2-fluoro-4-chloro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide

Product 1

HCID 17802075N-(2-fluoro-5-chlorocarbonyl-4-chlorophenyl)-2,3-dimethylmaleic acid imide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6 g of N-(2-fluoro-5-carboxy-4-chlorophenyl)-2,3-dimethylmaleic acid imide, 0.5 ml of dimethylmaleinimide, 2 ml of thionyl chloride and 50 ml of toluene is heated under reflux for 4 hours. After cooling, the whole is concentrated by evaporation in vacuo. 6 g of N-(2-fluoro-5-chlorocarbonyl-4-chlorophenyl)-2,3-dimethylmaleic acid imide having a melting point of 123°-124° are obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. concentrationthe whole is concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-ebdde2bcd03c4da9a40bc19c0fa3ea26
Source dataset
uspto-grants-1989_02
Patent number
US04804400

Reaction notes

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