Hydrochloric Acid → ethyl (3-chlorophenyl)carbamate

HRID 495636Notes

Reaction equation

HRID 495636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:11])[O:12][CH2:13][CH3:14])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79323-ChloroanilineHCID 10928Ethyl chloroformate

Product 1

HCID 247900ethyl (3-chlorophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Chloroaniline (2.510 g) was dissolved in pyridine (20 ml), and to the solution was added dropwise ethyl chloroformate (2.257 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 (3.9287 g, quantitative yield).

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-692c75bd73dd43c4b0495b1a0b0416bd
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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