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

HRID 496278Notes

Reaction equation

HRID 496278 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14].CCOC(C)=O.CCCCCC>N1C=CC=CC=1>[C:16]1([O:15][C:13](=[O:14])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:4][N:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 21226206Ethyl acetate hexane

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 2-amino-5-trifluoromethylpyridine (162 mg, 1.0 mmole) in pyridine (2.0 mL) under nitrogen at room temperature. Add drop wise phenyl chloroformate (0.125 mL, 1.0 mmole) to the reaction mixture at room temperature. Stir the mixture for 24 hours and new spot is noticed in TLC (30% EtOAc/hexane). Evaporate the reaction mixture under vacuo and purify the crude by flash column chromatography on a silica gel using CHCl3 to afford (5-Trifluoromethyl-pyridin-2-yl)-carbamic acid phenyl ester as a white solid. B. 1′-(5-Trifluoromethyl-pyridin-2-yl-carbamoyl)spiroisobenzofuran-1,4′-piperidine

Workup

  1. customEvaporate the reaction mixture under vacuo
  2. custompurify the crude by flash column chromatography on a silica gel

Sources & evidence

ORD record
ord-3f2820510d04447289709e6f976b251e
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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