Phosgene → Carbamic chloride, (2-phenoxyethyl)propyl-

HRID 262780Notes

Reaction equation

HRID 262780 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[O:5]([CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH3:17])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(OCC)(=O)C>[O:5]([CH2:12][CH2:13][N:14]([CH2:15][CH2:16][CH3:17])[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 6371Phosgene2×HCID 6453152N-(2-Phenoxyethyl)propylamine

Product 1

HCID 12238093Carbamic chloride, (2-phenoxyethyl)propyl-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 100 ml. of mechanically stirred, refluxing dry ethyl acetate was introduced a steady flow of phosgene gas followed by the dropwise addition of 22.4g. N-2-phenoxyethyl-N-propylamine in 100 ml. dry ethyl acetate over a period of 45 minutes. On completion of the addition, the reaction mixture was boiled under reflux with stirring, whilst continuing the flow of phosgene for a further three hours. The solvent was removed on the steam bath, the last traces being extracted under vacuum to give N-2-phenoxyethyl-N-propylcarbamoyl chloride.

Workup

  1. additionfollowed by the dropwise addition of 22.4g
  2. additionOn completion of the addition
  3. temperatureunder reflux
  4. stirringwith stirring
  5. customfor a further three hours
  6. customThe solvent was removed on the steam bath
  7. extractionthe last traces being extracted under vacuum

Sources & evidence

ORD record
ord-9e88e6ed3faf4be09918032205088e14
Source dataset
uspto-grants-1979_05
Patent number
US04154945

Reaction notes

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