Cyanide → HCID 21329847, compound

HRID 614023Notes

Reaction equation

HRID 614023 reaction equation
Cl[C:2]1C=CC(C(N=C=O)(C)C)=C[CH:3]=1.[C-]#N.C1(NO)C=CC=CC=1.[Cl:24][C:25]1[CH:44]=[CH:43][C:28]([C:29]([NH:32][C:33](=[O:42])[N:34]([OH:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([CH3:31])[CH3:30])=[CH:27][CH:26]=1.[O-]CC.[Na+].C(Br)C>C(OCC)C>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:32][C:33](=[O:42])[N:34]([O:41][CH2:2][CH3:3])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([CH3:30])[CH3:31])=[CH:43][CH:44]=1

Participants

8

Reactant 6

HCID 5975CyanideHCID 6332Ethyl BromideHCID 7518N-PhenylhydroxylamineHCID 2723922Sodium ethoxideHCID 131183231-Chloro-4-(2-isocyanatopropan-2-yl)benzeneHCID 21329850HCID 21329850, compound

Product 1

HCID 21329847HCID 21329847, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 19.6 g of p-chloro-α,α-dimethylbenzyl isocyanate, prepared from the corresponding cyanide in the same way as in Synthesis Example 1, in 10 ml of diethyl ether was added dropwise to a solution of 10.9 g of N-phenylhydroxylamine in 10 ml of diethyl ether. After completion of the addition, the mixture was stirred for 30 minutes whereby 3-(p-chloro-α,α-dimethylbenzyl)-1-hydroxy-1-phenylurea precipitated. The resulting crystals were separated by filtration and dried. A 3.0 g portion of the crystals thus obtained was added to 10 ml of an ethanolic solution of 750 mg of sodium ethoxide, and, after the crystals had been completely dissolved, 1.2 g of ethyl bromide was added thereto followed by heating at 60° C. for 2 hours. The solvent was then removed by distillation under reduced pressure, and the resulting residue was extracted with water and benzene. The benzene layer was washed successively with 2N aqueous sodium hydroxide and water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to precipitate crystals which were then recrystallized from a mixture of benzene and hexane to obtain 3.1 g of the title compound as white crystals.

Workup

  1. additionAfter completion of the addition
  2. customprecipitated
  3. customThe resulting crystals were separated by filtration
  4. customdried
  5. customA 3.0 g portion of the crystals thus obtained
  6. dissolutionafter the crystals had been completely dissolved
  7. customThe solvent was then removed by distillation under reduced pressure
  8. extractionthe resulting residue was extracted with water and benzene
  9. washThe benzene layer was washed successively with 2N aqueous sodium hydroxide and water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed by distillation
  12. customto precipitate crystals which
  13. customwere then recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-2dc722a734544e6fba8efe71e12088ef
Source dataset
uspto-grants-1979_03
Patent number
US04143061

Reaction notes

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