Cyanide → HCID 21329854, compound

HRID 614016Notes

Reaction equation

HRID 614016 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:5]([N:8]=[C:9]=[O:10])([CH3:7])[CH3:6].[C-]#N.[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:5]([NH:8][C:9](=[O:10])[N:18]([CH3:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 5975CyanideHCID 7515N-MethylanilineHCID 213298621,2-Dichloro-4-(2-isocyanatopropan-2-yl)benzene

Product 1

HCID 21329854HCID 21329854, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.6 g of 3,4-dichloro-α,α-dimethylbenzyl isocyanate, prepared from the corresponding cyanide in the same way as in Synthesis Example 1, was added to a solution of 2.2 g of N-methylaniline in 20 ml of benzene and the mixture was heated under reflux for 2 hours. After allowing the mixture to stand overnight, the reaction solution was washed with a 2N aqueous hydrochloric acid solution, a 2N aqueous sodium hydroxide solution and water in that order, and the organic layer was dried over sodium sulfate. The layer was concentrated by evaporating off the solvent to obtain crystals, which were recrystallized from n-hexane to obtain 5.8 g of the title compound as crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washthe reaction solution was washed with a 2N aqueous hydrochloric acid solution
  4. dry with materiala 2N aqueous sodium hydroxide solution and water in that order, and the organic layer was dried over sodium sulfate
  5. concentrationThe layer was concentrated
  6. customby evaporating off the solvent
  7. customto obtain crystals, which
  8. customwere recrystallized from n-hexane

Sources & evidence

ORD record
ord-64fb70389af14900afa269db32f35d9d
Source dataset
uspto-grants-1979_03
Patent number
US04143061

Reaction notes

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