Benzyl Isothiocyanate → 3-Benzyl-1-{4-[2-(4-chlorobenzoyl)hydrazino]phenyl}thiourea

HRID 437303Notes

Reaction equation

HRID 437303 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.[CH2:20]([N:27]=[C:28]=[S:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(=O)C.[K+]>C(O)C.O>[CH2:20]([NH:27][C:28](=[S:29])[NH:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][NH:9][C:7](=[O:8])[C:6]2[CH:18]=[CH:19][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:12][CH:13]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 2346Benzyl IsothiocyanateHCID 517044Potassium AcetateHCID 214278261-(4-Chlorobenzoyl)-2-(4-aminophenyl)hydrazine hydrochloride

Product 1

HCID 214278283-Benzyl-1-{4-[2-(4-chlorobenzoyl)hydrazino]phenyl}thiourea

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(4-Chlorobenzoyl)-2-(4-aminophenyl)hydrazine hydrochloride (1.5 g, 0.005 mole) was dissolved in hot ethanol (30 ml) under a nitrogen atmosphere. Benzyl isothiocyanate (0.82 g, 0.0055 mole) and potassium acetate (0.6 g, 0.006 mole) were added and the mixture was refluxed under nitrogen for two hours. The reaction mixture was cooled to room temperature, diluted with water (10-15ml.) and chilled in ice. The product was filtered off, washed with ethanol and dried. Recrystallization of the product from acetonitrile gave an off-white solid. Yield 1.25 g (62%), m.p. 197°-199° C.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for two hours
  2. temperaturechilled in ice
  3. filtrationThe product was filtered off
  4. washwashed with ethanol
  5. customdried
  6. customRecrystallization of the product from acetonitrile
  7. customgave an off-white solid

Sources & evidence

ORD record
ord-475e63bf55054847bb92a0909d706045
Source dataset
uspto-grants-1977_06
Patent number
US04030925

Reaction notes

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