Water → 2,2,2-Trichloroethyl[6-(acetylamino)pyridin-3-yl]carbamate

HRID 2263043Notes

Reaction equation

HRID 2263043 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20].O>O1CCCC1>[C:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 27352192-Acetamido-5-aminopyridine

Product 1

HCID 862452592,2,2-Trichloroethyl[6-(acetylamino)pyridin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-aminopyridin-2-yl)acetamide (1.00 g, 6.62 mmol) and pyridine (0.647 ml, 7.94 mmol) in tetrahydrofuran (22 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.10 ml, 7.94 mmol), and the mixture was stirred at room temperature for 2 hours. Water was poured to the reaction mixture, and the resulting solution 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. Hexane was poured to the residue, and 1.47 g (68.1%) of the desired product as a solid was separated by filtration.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was poured to the residue, and 1.47 g (68.1%) of the desired product as a solid
  7. customwas separated by filtration

Sources & evidence

ORD record
ord-cc19011fbbed4ad6a2fbb56c76a3e0b0
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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