Water → HCID 13073056, compound

HRID 1263053Notes

Reaction equation

HRID 1263053 reaction equation
[Cl:1][C:2]1[C:3]([O:5][C:6](=[O:9])[C:7]=1[Cl:8])=O.[F:10][CH:11]([F:20])[O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.O>C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:6]([N:17]([C:16]2[CH:18]=[CH:19][C:13]([O:12][CH:11]([F:10])[F:20])=[CH:14][CH:15]=2)[C:3](=[O:5])[C:2]=1[Cl:1])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 70728Dichloromaleic anhydrideHCID 7373634-(Difluoromethoxy)aniline

Product 1

HCID 13073056HCID 13073056, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 16.7 g (0.1 mole) of 2,3-dichloromaleic anhydride in 70 ml of toluene is heated to boiling. A solution of 15.9 g (0.1 mole) of p-difluoromethoxyaniline in 30 ml of toluene is added dropwise to it over 20 minutes with stirring. Thereafter, the resulting solution is refluxed until water is no longer distilled. This requires about 2 hours. The mixture is cooled to room temperature to precipitate crystals. The precipitated crystals are filtered off and washed with hexane to obtain 29.2 g of 2,3-dichloro-N-(p-difluoromethoxyphenyl)maleimide melting at 217.5°-218° C. in the form of light yellow plate crystals.

Workup

  1. distillationis no longer distilled
  2. customThis requires about 2 hours
  3. customto precipitate crystals
  4. filtrationThe precipitated crystals are filtered off
  5. washwashed with hexane

Sources & evidence

ORD record
ord-b9f7cc4354374a92a95e79717a9ab674
Source dataset
uspto-grants-1984_06
Patent number
US04455315

Reaction notes

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