Malonamide → 6-(1-Chloro-1,2,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 512481

Reaction equation

HRID 512481 reaction equation
[Na].C(O[CH:7]=[CH:8][C:9](=O)[C:10]([Cl:16])([F:15])[C:11]([F:14])([F:13])[F:12])CCC.[C:18]([NH2:24])(=[O:23])[CH2:19][C:20]([NH2:22])=[O:21]>CO>[Cl:16][C:10]([C:9]1[NH:22][C:20](=[O:21])[C:19]([C:18]([NH2:24])=[O:23])=[CH:7][CH:8]=1)([F:15])[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 7911MalonamideHCID 5360545SodiumHCID 866240961-Butoxy-4-chloro-4,5,5,5-tetrafluoropent-1-en-3-one

Product 1

HCID 598282486-(1-Chloro-1,2,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.33 g (14.4 mmol) of sodium were dissolved in 50 ml of methanol, 3.16 g (12.03 mmol) of 1-butoxy-4-chloro-4,5,5,5-tetrafluoropent-1-en-3-one and 1.27 g (12.03 mmol) of malonamide were added and the mixture was heated under reflux for 7 h. The mixture was concentrated, and 1N hydrochloric acid was then added. The resulting precipitate was filtered off with suction and dried. This gave 380 mg (12% of theory) of a yellowish powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 h
  3. concentrationThe mixture was concentrated
  4. addition1N hydrochloric acid was then added
  5. filtrationThe resulting precipitate was filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-0fdb4360d4fe4d69a30d537b9be032cc
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Linked notes

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