Cyanide → 3-(m-Chloro-alpha,alpha-dimethylbenzyl)-1-cyclohexyl-1-methylurea

HRID 614015Notes

Reaction equation

HRID 614015 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[C:13]([N:16]=[C:17]=[O:18])([CH3:15])[CH3:14].[C-]#N>CCCCCC.C1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][CH:21]=1)[C:13]([NH:16][C:17](=[O:18])[N:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:1])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 5975CyanideHCID 7514N-MethylcyclohexylamineHCID 213298491-Chloro-3-(2-isocyanatopropan-2-yl)benzene

Product 1

HCID 213298393-(m-Chloro-alpha,alpha-dimethylbenzyl)-1-cyclohexyl-1-methylureaYield 90.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.2 g of N-methyl-N-cyclohexylamine in 5 ml of n-hexane was added to a solution of 0.01 mole of m-chloro-α,α-dimethylbenzyl isocyanate (prepared from the corresponding cyanide in the same way as shown in Synthesis Example 1) in 10 ml of benzene. The mixture was kept at room temperature for 6 hours and concentrated under reduced pressure to obtain crystals, which were recrystallized from n-hexane to give 2.8 g of the title compound as white crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto obtain crystals, which
  3. customwere recrystallized from n-hexane

Sources & evidence

ORD record
ord-38dc2c6bcd744c38b6d1f74a83f09570
Source dataset
uspto-grants-1979_03
Patent number
US04143061

Reaction notes

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