Phenyl chloroformate → Phenyl [5-(trifluoromethyl)pyridin-2-yl]carbamate

HRID 2396571Notes

Reaction equation

HRID 2396571 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=1>N1C=CC=CC=1>[F:21][C:18]([F:19])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 11426042Phenyl [5-(trifluoromethyl)pyridin-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
21 °C

Procedure

Phenyl chloroformate (1.92 g, 12.3 mmol) was added to a stirring solution of 2-amino-5-trifluoromethylpyridine (2.0 g, 12.3 mmol) in pyridine (20 mL) at a rate which maintained the temperature at 21° C. The mixture was stirred for an additional 0.5 hr and the resulting precipitate was collected by filtration, extracted with ether, then dried to obtain 2.33 g (67 percent of theory) of the title compound as white crystals melting at 203° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. extractionextracted with ether
  3. customdried

Sources & evidence

ORD record
ord-c6e48de4ad0b455b878d2c5ce3914c24
Source dataset
uspto-grants-1996_02
Patent number
US05493024

Reaction notes

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