Hydrochloric Acid → Ethyl 2-chlorophenylcarbamate

HRID 495611

Reaction equation

HRID 495611 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:11])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 72402-ChloroanilineHCID 10928Ethyl chloroformate

Product 1

HCID 528085Ethyl 2-chlorophenylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chloroaniline (1.4463 g) was dissolved in pyridine (10 ml), and to the solution was added dropwise ethyl chloroformate (1.30 ml) under ice-cooling. After the mixture was stirred for 1 hour, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (2.2203 g, 98%).

Workup

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

Sources & evidence

ORD record
ord-20e2a6910ef245dda1b9bea78eba1ec0
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Linked notes

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