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

HRID 2263101Notes

Reaction equation

HRID 2263101 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])=[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]>O1CCCC1>[Cl:25][C:24]([Cl:27])([Cl:26])[CH2:23][O:22][C:20](=[O:21])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9](=[O:11])[CH3:10])[CH3:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67068N-(4-Aminophenyl)-N-methylacetamideHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 866254962,2,2-Trichloroethyl {4-[acetyl(methyl)amino]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-aminophenyl)-N-methylacetamide (1.78 g, 10.8 mmol) and pyridine (2.63 ml, 32.5 mmol) in tetrahydrofuran (60 ml) was added 2,2,2-trichloroethyl chloroformate (2.23 ml, 16.2 mmol) with ice-cooling, the mixture was stirred for 2 hours with ice-cooling, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. To the residue was added hexane and the desired product (3.17 g, 86.4%) as a solid was collected by filtration.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the residue was added hexane
  8. filtrationthe desired product (3.17 g, 86.4%) as a solid was collected by filtration

Sources & evidence

ORD record
ord-139c6dd54c50421692567f010160ecea
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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