Hydrochloric Acid → 5-Chloro-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

HRID 512460Notes

Reaction equation

HRID 512460 reaction equation
S(Cl)(Cl)(=O)=O.[O:6]=[C:7]1[C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=[C:9]([C:16]([F:19])([F:18])[F:17])[NH:8]1.[ClH:20]>ClCCCl.N1C=CC=CC=1>[Cl:20][C:10]1[CH:11]=[C:12]([C:13]([NH2:15])=[O:14])[C:7](=[O:6])[NH:8][C:9]=1[C:16]([F:17])([F:19])[F:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24648Sulfuryl chlorideHCID 27751142-Hydroxy-6-(trifluoromethyl)nicotinamide

Product 1

HCID 598282345-Chloro-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1049PyridineSolvent

Procedure

At room temperature, 0.39 g (2.9 mmol) of sulfuryl chloride was added to 300 mg (1.46 mmol) of 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide in 5 ml of 1,2-dichloroethane and 2.3 g (0.25 ml) of pyridine, and the mixture was then heated under reflux for 2 h. The mixture was then added to 0.5N hydrochloric acid. The organic phase was removed and then dried and concentrated, which gave 144 mg (41% of theory) of a brownish powder.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 2 h
  3. customThe organic phase was removed
  4. customdried
  5. concentrationconcentrated
  6. customwhich gave 144 mg (41% of theory) of a brownish powder

Sources & evidence

ORD record
ord-cb1f19f9b88b43218886e9c0b6ae51a8
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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