Phenyl Isothiocyanate → N-Butan-2-yl-N-[(4-chlorophenyl)methyl]-N'-phenylthiourea

HRID 259285Notes

Reaction equation

HRID 259285 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH:8]([CH2:10][CH3:11])[CH3:9])=[CH:4][CH:3]=1.[C:14]1([N:20]=[C:21]=[S:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH:8]([CH2:10][CH3:11])[CH3:9])[C:21]([NH:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[S:22])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 4717029N-(4-chlorobenzyl)butan-2-amine

Product 1

HCID 13018270N-Butan-2-yl-N-[(4-chlorophenyl)methyl]-N'-phenylthioureaYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

20 g of N-(4-chlorobenzyl)-N-sec.-butylamine were dissolved in 500 ml of ether. To the resulting solution, a solution of 14 g of phenyl isothiocyanate in 50 ml of ether was added dropwise, under cooling and stirring. After the dropwise addition, the temperature of the solution was gradually raised, and the solution was then stirred at room temperature for about 10 hours. The crystals which had been formed were separated by filtration. After recrystallization with a solvent mixture of hexane and ethyl alcohol, 30 g of N-(4-chlorobenzyl)-N-sec.-butyl-N'-phenylthiourea were obtained. Yield: 91%. Melting point: 134°-134.5° C.

Workup

  1. temperatureunder cooling
  2. additionAfter the dropwise addition
  3. temperaturethe temperature of the solution was gradually raised
  4. stirringthe solution was then stirred at room temperature for about 10 hours
  5. customThe crystals which had been formed
  6. customwere separated by filtration
  7. customAfter recrystallization
  8. additionwith a solvent mixture of hexane and ethyl alcohol

Sources & evidence

ORD record
ord-8fee94989e1f483d8687b053b84066cc
Source dataset
uspto-grants-1977_07
Patent number
US04036986

Reaction notes

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