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

HRID 437525Notes

Reaction equation

HRID 437525 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 2 hours. The reaction mixture was cooled to room temperature, diluted with water (10-15 ml.) 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 2 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-96f4a1d08c0b4bdabafb7d5b2fee3fb8
Source dataset
uspto-grants-1977_06
Patent number
US04031127

Reaction notes

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