Phosgene → tert-Butyl(ethenyl)carbamyl chloride

HRID 2163832Notes

Reaction equation

HRID 2163832 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH:5](=[N:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:6].CN(C)C1CCCCC1.Cl.CN(C)C1CCCCC1>O.C(Cl)Cl>[CH:5]([N:7]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:1]([Cl:4])=[O:2])=[CH2:6]

Participants

7

Reactant 4

HCID 6371Phosgene2×HCID 7415N,N-DimethylcyclohexylamineHCID 102275N,N-Dimethylcyclohexanamine--hydrogen chloride (1/1)HCID 138901N-Ethylidene-2-methylpropan-2-amine

Product 1

HCID 12573481tert-Butyl(ethenyl)carbamyl chlorideYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

60 parts of phosgene are introduced into 224 parts of methylene chloride. 39.6 parts of ethylidene-tert.-butylamine, 51 parts of dimethylcyclohexylamine and 210 parts of methylene chloride are added to this solution in the course of one hour at from 0° to 5° C., whilst stirring. The mixture is then stirred for 30 minutes, after which the reaction solution is freed from excess phosgene. The mixture is now thoroughly mixed with 250 parts of water at 0° C., whereupon the dimethylcyclohexylamine hydrochloride passes into the aqueous phase. This aqueous phase is separated off and neutralized with sodium hydroxide solution, and the dimethylcyclohexylamine is recovered by distillation. The organic phase is distilled. 52 parts of N-vinyl-N-tert.-butylcarbamoyl chloride (80% of theory) boiling at 85° C./14 mm Hg are obtained.

Workup

  1. stirringThe mixture is then stirred for 30 minutes
  2. customThis aqueous phase is separated off
  3. distillationthe dimethylcyclohexylamine is recovered by distillation
  4. distillationThe organic phase is distilled

Sources & evidence

ORD record
ord-b0e4baab3397460bad70166d4de4a515
Source dataset
uspto-grants-1979_01
Patent number
US04137261

Reaction notes

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