Cyanide → 3-(p-Chloro-alpha,alpha-dimethylbenzyl)-1-ethyl-1-phenylurea

HRID 614022Notes

Reaction equation

HRID 614022 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:9]=[C:10]=[O:11])([CH3:8])[CH3:7])=[CH:4][CH:3]=1.[C-]#N.[CH2:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:17]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:9][C:10](=[O:11])[N:18]([CH2:16][CH3:17])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH3:8])[CH3:7])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 5975CyanideHCID 7670N-EthylanilineHCID 131183231-Chloro-4-(2-isocyanatopropan-2-yl)benzene

Product 1

HCID 213298613-(p-Chloro-alpha,alpha-dimethylbenzyl)-1-ethyl-1-phenylureaYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.9 g of p-chloro-α,α-dimethylbenzyl isocyanate, prepared from the corresponding cyanide in the same way as in Synthesis Example 1, in 20 ml of toluene was added to 2.7 g of N-ethylaniline and the mixture was heated under reflux for 3 hours. After allowing the reaction mixture to cool, the mixture was washed successively with 2N hydrochloric acid, 2N aqueous sodium hydroxide and water. The organic layer was dried over anhydrous sulfate and the solvent was removed by distillation under reduced pressure to obtain 6.2 g of the title compound as a light brown oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. washthe mixture was washed successively with 2N hydrochloric acid, 2N aqueous sodium hydroxide and water
  5. dry with materialThe organic layer was dried over anhydrous sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3d4c616b4bdf4b13a29d018948a15c8d
Source dataset
uspto-grants-1979_03
Patent number
US04143061

Reaction notes

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