Phenyl Isothiocyanate → 1-[4-(2-Acetylhydrazino)phenyl]-3-phenylthiourea

HRID 437293Notes

Reaction equation

HRID 437293 reaction equation
[C:1]([NH:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[C:13]1([N:19]=[C:20]=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[C:1]([NH:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:20]([NH:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[S:21])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 81068Acetic acid, 2-(4-aminophenyl)hydrazide

Product 1

HCID 214278081-[4-(2-Acetylhydrazino)phenyl]-3-phenylthiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Acetyl-2-(4-aminophenyl)hydrazine (8.25 g, 0.05 mole) and phenyl isothiocyanate (6.8 g, 0.05 mole) were suspended in acetonitrile (100 ml). The resulting mixture was heated at reflux with stirring for 5 minutes. The product separated from solution as a white solid. After chilling, the product was removed from the reaction mixture by filtration and washed thoroughly with ether. Yield 14.5 g (96%), m.p. 205°-207° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux
  3. customThe product separated from solution as a white solid
  4. temperatureAfter chilling
  5. customthe product was removed from the reaction mixture by filtration
  6. washwashed thoroughly with ether

Sources & evidence

ORD record
ord-a7b5c2b53aa04f22ac27f81cac58c183
Source dataset
uspto-grants-1977_06
Patent number
US04030925

Reaction notes

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