Hydrochloric Acid → Ethyl (3-chlorophenyl)carbamate
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with 1N hydrochloric acid
- dry with materialsaturated brine, dried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-692c75bd73dd43c4b0495b1a0b0416bd
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06939887B2
Reaction notes
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