Phenylhydrazine → 1-Anilino-3-chloro-4-phenylpyrrol-2,5-dione

HRID 1355333Notes

Reaction equation

HRID 1355333 reaction equation
[Cl:1][C:2]1[C:3](=[O:14])O[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:15]1([NH:21][NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[NH:21]([N:22]1[C:5](=[O:13])[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:2]([Cl:1])[C:3]1=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 234471953-Chloro-4-phenylfuran-2,5-dione

Product 1

HCID 98147801-Anilino-3-chloro-4-phenylpyrrol-2,5-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.14 g (20 mmol) of 3-chloro-4-phenylfuran-2,5-dione were initially charged in 50 ml of chloroform and, at room temperature, admixed dropwise with stirring with 2.16 g (20 mmol) of phenyl hydrazine, and the mixture was stirred at room temperature overnight. The mixture was filtered, washed three times with sodium bicarbonate solution and once with water, dried over sodium sulfate and concentrated under reduced pressure. Yield: 5.4 g of a crystalline solid, m.p. 144-146° C.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed three times with sodium bicarbonate solution
  3. dry with materialonce with water, dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84cffaffff104a36a6407cf35937fc27
Source dataset
uspto-grants-2003_07
Patent number
US06586369B1

Reaction notes

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