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

HRID 437305Notes

Reaction equation

HRID 437305 reaction equation
[C:1]([NH:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[C:22]1([N:28]=[C:29]=[S:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C.O>[C:1]([NH:4][NH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:29]([NH:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[S:30])=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 214278101-Acetyl-2-[4-(4-methoxybenzyl)aminophenyl]hydrazine

Product 1

HCID 214278371-[4-(2-Acetylhydrazino)phenyl]-1-(4-methoxybenzyl)-3-phenylthiourea

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Acetyl-2-[4-(4-methoxybenzyl)aminophenyl]hydrazine (3.1 g, 0.011 mole) and phenylisothiocyanate (1.35 g, 0.01 mole) were mixed in ethanol (25 ml) and the resulting mixture was refluxed for 10 minutes. The mixture was chilled in ice and diluted with water. The product oiled out of solution, but upon standing and scratching the substance solidified. The solid material was filtered off, washed with water and allowed to dry. The material was stirred twice in a large volume of ether, then was filtered and washed with fresh ether. The product was a white powder. Yield 2.75 g (66%), m.p. 126°-128° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 10 minutes
  2. temperatureThe mixture was chilled in ice
  3. filtrationThe solid material was filtered off
  4. washwashed with water
  5. customto dry
  6. filtrationwas filtered
  7. washwashed with fresh ether

Sources & evidence

ORD record
ord-3b90f155ba78432085337fb2e973aa48
Source dataset
uspto-grants-1977_06
Patent number
US04030925

Reaction notes

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