Dichloromaleic anhydride → HCID 13073055, compound

HRID 1263052Notes

Reaction equation

HRID 1263052 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:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16]>O1CCOCC1>[Cl:8][C:7]1[C:6]([N:16]([C:15]2[CH:17]=[CH:18][CH:19]=[C:13]([O:12][CH:11]([F:10])[F:20])[CH:14]=2)[C:3](=[O:5])[C:2]=1[Cl:1])=[O:9]

Participants

4

Reactant 2

HCID 70728Dichloromaleic anhydrideHCID 27741103-(Difluoromethoxy)aniline

Product 1

HCID 13073055HCID 13073055, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

16.7 g (0.1 mole) of 2,3-dichloromaleic anhydride is dissolved in 100 ml of dioxane, and a solution of 15.9 g (0.1 mole) of m-difluoromethoxyaniline in 30 ml of dioxane is added dropwise to it at room temperature over 20 minutes with stirring. Thereafter, the resulting solution is stirred at 70°-80° C. for 2 hours and the dioxane is then distilled off under a reduced pressure. Water is added to the residue to precipitate crystals. The precipitated crystals are filtered off and recrystallized to give 29.2 g (yield: 95%) of 2,3-dichloro-N-(m-difluoromethoxyphenyl)maleimide melting at 122°-124° C. in the form of light yellow plate crystals.

Workup

  1. stirringThereafter, the resulting solution is stirred at 70°-80° C. for 2 hours
  2. distillationthe dioxane is then distilled off under a reduced pressure
  3. additionWater is added to the residue
  4. customto precipitate crystals
  5. filtrationThe precipitated crystals are filtered off
  6. customrecrystallized

Sources & evidence

ORD record
ord-659000ad08e947b78939a449b6b7d3b9
Source dataset
uspto-grants-1984_06
Patent number
US04455315

Reaction notes

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