Pyridine → 2,2,2-Trichloroethyl {4-[(trifluoroacetyl)amino]phenyl}carbamate

HRID 2263246Notes

Reaction equation

HRID 2263246 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)=[O:4].N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]>CN(C)C(=O)C>[F:1][C:2]([F:13])([F:14])[C:3]([NH:5][C:6]1[CH:12]=[CH:11][C:9]([NH:10][C:22](=[O:23])[O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 6750874-Trifluoroacetamidoaniline

Product 1

HCID 866255142,2,2-Trichloroethyl {4-[(trifluoroacetyl)amino]phenyl}carbamateYield 96.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-trifluoroacetylaminoaniline (1.00 g, 4.90 mmol) and pyridine (1.20 ml, 15.0 mmol) in N,N-dimethylacetamide (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.01 ml, 7.35 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 2 hours. The reaction mixture was poured into ice-water, and a solid was collected by filtration to give 1.80 g (96.8%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hours
  3. filtrationa solid was collected by filtration

Sources & evidence

ORD record
ord-22543ae751414d9580e853d6daf9a76a
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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