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

HRID 2263107Notes

Reaction equation

HRID 2263107 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:11])=[O:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20]>O1CCCC1>[O:10]=[C:9]([CH3:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 117883794-Aminophenylacetone

Product 1

HCID 862450662,2,2-Trichloroethyl [4-(2-oxopropyl)phenyl]carbamateYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-aminophenyl)acetone (1.13 g, 7.57 mmol) and pyridine (1.84 ml, 22.7 mmol) in tetrahydrofuran (50 ml) was added 2,2,2-trichloroethyl chloroformate (1.57 ml, 11.4 mmol) with ice-cooling, and the mixture was stirred for 1 hour with ice-cooling and then at room temperature for 1 hour, 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. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1) to obtain the desired product (1.44 g, 58.4%) as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitat room temperature for 1 hour
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6e6ebfff9c844a61aa26228e434e60bd
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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