Ethanol → 1-{4-[2-(4-Chlorobenzoyl)hydrazino]phenyl}-3-phenylthiourea

HRID 437524Notes

Reaction equation

HRID 437524 reaction equation
Cl.[Cl:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[O:8])=[CH:5][CH:4]=1.C(O)C.[C:23]1([N:29]=[C:30]=[S:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[Na+]>O>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:30]([NH:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[S:31])=[CH:13][CH:12]=2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7673Phenyl IsothiocyanateHCID 517045Sodium AcetateHCID 214278261-(4-Chlorobenzoyl)-2-(4-aminophenyl)hydrazine hydrochloride

Product 1

HCID 214278401-{4-[2-(4-Chlorobenzoyl)hydrazino]phenyl}-3-phenylthiourea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-(4-Chlorobenzoyl)-2-(4-aminophenyl)hydrazine hydrochloride (2.0 g, 0.0067 mole) was mixed with ethanol (125 ml) and water (25ml). Phenyl isothiocyanate (1.1 g, 0.01 mole) was added to the mixture along with sodium acetate (0.82 g, 0.1 mole) in water (10 ml). The reaction mixture was stirred and refluxed for 5 minutes, then was stirred at room temperature for 11/2 hours. The mixture was chilled in ice and then filtered. The product was washed with ethanol and dried to give an off-white solid. Yield 1.9 g (71%), m.p. 197.5°-199° C.

Workup

  1. temperaturerefluxed for 5 minutes
  2. stirringwas stirred at room temperature for 11/2 hours
  3. temperatureThe mixture was chilled in ice
  4. filtrationfiltered
  5. washThe product was washed with ethanol
  6. customdried
  7. customto give an off-white solid

Sources & evidence

ORD record
ord-529f78032edf41abbf0ac2f7f7859588
Source dataset
uspto-grants-1977_06
Patent number
US04031127

Reaction notes

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