Phosgene → N-(2-methoxyethyl)-N-ethylcarbamoyl chloride

HRID 1606097Notes

Reaction equation

HRID 1606097 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH2:5]([NH:7][CH2:8][CH2:9][O:10][CH3:11])[CH3:6]>CCOCC>[CH3:11][O:10][CH2:9][CH2:8][N:7]([CH2:5][CH3:6])[C:1]([Cl:4])=[O:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 546877N-(2-Methoxyethyl)ethylamine

Product 1

HCID 12238060N-(2-methoxyethyl)-N-ethylcarbamoyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 89.1 g. phosgene in 500 ml. dry ether at -20°C. was added a solution of 30.9 g. N-ethyl-N-2-methoxyethylamine in 50 ml. dry ether, whilst the temperature of the reaction mixture was maintained at -20°C. The stirred mixture was then allowed to warm to room temperature during 1 hour. The reaction mixture was filtered and the filtrate evaporated in vacuo below 25°C. to remove the solvent and give the product, N-(2-methoxyethyl)-N-ethylcarbamoyl chloride as a pale yellow liquid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated in vacuo below 25°C.
  3. customto remove the solvent

Sources & evidence

ORD record
ord-d46605da359f4d09a3bd358b7176a6d1
Source dataset
uspto-grants-1976_04
Patent number
US03952001

Reaction notes

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