Hydrochloric Acid → Ethyl 2-chlorobenzylcarbamate

HRID 495617Notes

Reaction equation

HRID 495617 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:11](=[O:12])[O:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 666482-Chlorobenzylamine

Product 1

HCID 22327377Ethyl 2-chlorobenzylcarbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chlorobenzylamine (1.7734 g) was dissolved in pyridine (10 ml), and to the solution was added dropwise ethyl chloroformate (1.437 ml) during 20 minutes under ice-cooling. After the mixture was stirred for 40 minutes, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (2.715 g, quantitative yield).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution
  4. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-45d90d5d5c144788be725884810753e9
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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