Ethyl chloroformate → Carbamic acid, bis(2-chloroethyl)-, ethyl ester

HRID 1670753Notes

Reaction equation

HRID 1670753 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CC(C)=O>[Cl:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][Cl:8])[C:16](=[O:17])[O:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 21635Carbamic acid, bis(2-chloroethyl)-, ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

bis(2-Chloroethyl)amine hydrochloride (Tokyo Chemical Industry CO., LTD., 3.0 g) was dissolved in acetone (50 ml), potassium carbonate (3.0 g) and ethyl chloroformate (2.4 ml) were added, and the mixture was heated under reflux for 4 hr. After completion of the reaction, the mixture was cooled to room temperature, and the solid was filtered off. The filtrate was evaporated under reduced pressure to give ethyl bis(2-chloroethyl)carbamate (3.7 g, yield 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. customAfter completion of the reaction
  4. filtrationthe solid was filtered off
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-74d02eb6f29a48eba2d4cf759079669f
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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