Pyridine → 2,2,2-Trichloroethyl [4-(propionylamino)phenyl]carbamate

HRID 2263237Notes

Reaction equation

HRID 2263237 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10][CH3:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21]>CN(C)C(=O)C>[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:20](=[O:21])[O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[CH:7][CH:6]=1)(=[O:12])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 314342N-(4-Aminophenyl)propanamide

Product 1

HCID 866255132,2,2-Trichloroethyl [4-(propionylamino)phenyl]carbamateYield 97.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-(4-aminophenyl)propanamide (2.00 g, 10.3 mmol) and pyridine (2.50 ml, 30.9 mmol) in N,N-dimethylacetamide (40 ml) was added 2,2,2-trichloroethyl chloroformate (2.13 ml, 15.5 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 2 hours. The reaction mixture was poured into ice-water, and 3.41 g (97.4%) of the desired product was collected by filtration as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hours

Sources & evidence

ORD record
ord-198ba61545dc4c4f88ac90dd4f2c964f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

Loading…