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

HRID 437513Notes

Reaction equation

HRID 437513 reaction equation
[C:1]([NH:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([N:24]=[C:25]=[S:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[C:1]([NH:9][NH:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:25]([NH:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[S:26])=[CH:15][CH:16]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 20508846N'-(4-Aminophenyl)benzohydrazide

Product 1

HCID 214278351-[4-(2-Benzoylhydrazino)phenyl]-3-phenylthiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Benzoyl-2-(4-aminophenyl)hydrazine (1.14 g, 0.005 mole) and phenyl isothiocyanate (2.7 g, 0.02 mole) were mixed together and heated until contents became fluid. Gentle warming was continued for a few minutes and the reaction mixture was then chilled and diluted with ether. After some stirring and scratching, the product precipitated from solution. It was filtered off, washed thoroughly with ether and dried. Yield 1.7 g (94%), m.p. 149°-151° C.

Workup

  1. temperatureheated until contents
  2. temperatureGentle warming
  3. waitwas continued for a few minutes
  4. temperaturethe reaction mixture was then chilled
  5. customthe product precipitated from solution
  6. filtrationIt was filtered off
  7. washwashed thoroughly with ether
  8. customdried

Sources & evidence

ORD record
ord-849c89fc4dfe4219b3810d1c35837e13
Source dataset
uspto-grants-1977_06
Patent number
US04031127

Reaction notes

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