Phenylhydrazine → HCID 10268972, compound

HRID 1840251Notes

Reaction equation

HRID 1840251 reaction equation
[Br: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]([Br: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 12397650HCID 12397650, compound

Product 1

HCID 10268972HCID 10268972, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4.3 g (17 mmol) of 3-bromo-4-phenylfuran-2,5-dione were initially charged in 40 ml of chloroform and, at room temperature, admixed dropwise with stirring with 1.84 g (17 mmol) of phenylhydrazine in 15 ml of chloroform, and the mixture was stirred at room temperature overnight. The mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography using ethyl acetate/cyclohexane. Yield: 1.9 g, m.p. 146-147° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-36648a3de715408fb363bdd2c840a2a8
Source dataset
uspto-grants-2004_01
Patent number
US06680283B1

Reaction notes

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