Phenyl isocyanate → HCID 13018269, compound

HRID 596307Notes

Reaction equation

HRID 596307 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]=[O: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)=[O:22])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 4717029N-(4-chlorobenzyl)butan-2-amine

Product 1

HCID 13018269HCID 13018269, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

30 g (0.15 mole) of N-(4-chlorobenzyl)N-sec.-butylamine were dissolved in 500 ml of ether. To the resulting solution, a solution of 18 g (0.15 mole) of phenyl isocyanate 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, 44 g of N-(4-chlorobenzyl)-N-sec.-butyl-N'-phenylurea were obtained. Yield: 93%. Melting point: 80°-81.5° 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-3b5ad136fafb44e4b42c8437085d5c4a
Source dataset
uspto-grants-1977_03
Patent number
US04010281

Reaction notes

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