Phosgene → Benzyl(butyl)carbamyl chloride

HRID 2418686Notes

Reaction equation

HRID 2418686 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH2:5]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH2:5]([N:12]([CH2:13][CH2:14][CH2:15][CH3:16])[C:1]([Cl:4])=[O:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 75467Benzenemethanamine, N-butyl-

Product 1

HCID 13339983Benzyl(butyl)carbamyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 20.0 g of phosgene in 100 ml. of toluene is stirred at 0° C. while a solution of 32.6 g. of N-benzyl-n-butylamine in 50 ml. of toluene is added during 15 minutes. The mixture is filtered and the filtrate is evpaorated. The residue is evaporatively distilled at 105° C. under reduced pressure (250-350 microns) to yield N-benzyl-N-(n-butyl)carbamyl chloride as a colorless liquid.

Workup

  1. filtrationThe mixture is filtered
  2. distillationThe residue is evaporatively distilled at 105° C. under reduced pressure (250-350 microns)

Sources & evidence

ORD record
ord-226446775aa74a5e854fe213b7baefc2
Source dataset
uspto-grants-1984_09
Patent number
US04473579

Reaction notes

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