Phosgene → Di-sec-butylcarbamoyl chloride

HRID 622325Notes

Reaction equation

HRID 622325 reaction equation
[CH:1]([NH:5][CH:6]([CH2:8][CH3:9])[CH3:7])([CH2:3][CH3:4])[CH3:2].[C:10](Cl)([Cl:12])=[O:11]>ClC1C=CC=CC=1>[CH:1]([N:5]([CH:6]([CH2:8][CH3:9])[CH3:7])[C:10]([Cl:12])=[O:11])([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 12277DI-Sec-butylamine

Product 1

HCID 3015862Di-sec-butylcarbamoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 129.0 g of di-sec.-butylamine and 129.0 g of chlorobenzene was reacted with phosgene in accordance with Example 1. When the phosgenation was complete, the mixture was heated under reflux for a further hour, the residual phosgene was then removed by blowing out with nitrogen, and, after the solvent had been removed under a moderate vacuum, the main product was collected by distillation. N,N-di-sec.-butylcarbamoyl chloride was obtained in this manner in a yield of 186.0 g and in a purity of 99.8%. The yield of 100% strength carbamoyl chloride was 185.6 g, corresponding to 96.9% of theory. A residue of 2.5 g (corresponding to 1.2% of the theoretical yield) remained in the distillation flask.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for a further hour
  3. customthe residual phosgene was then removed
  4. customafter the solvent had been removed under a moderate vacuum
  5. distillationthe main product was collected by distillation

Sources & evidence

ORD record
ord-9b558a9ad9634037871e442f6f458e03
Source dataset
uspto-grants-1988_09
Patent number
US04770820

Reaction notes

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