Citric Acid → HCID 15457060, compound

HRID 992876Notes

Reaction equation

HRID 992876 reaction equation
C([S:4][C:5]1[C:6]([Cl:24])=[CH:7][C:8]([F:23])=[C:9]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[CH:10]=1)(=O)C.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[Cl:24][C:6]1[C:5]([SH:4])=[CH:10][C:9]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)=[C:8]([F:23])[CH:7]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15457059HCID 15457059, compound

Product 1

HCID 15457060HCID 15457060, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.8 g (7.7 mmol) of 3-(5-acetylthio-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 30 ml of methanol, 8.5 ml (8.5 mmol) of a 1N sodium hydroxide aqueous solution was dropwise added thereto under cooling with ice. After stirring at room temperature for 1 hour, the mixture was poured into water and acidified with citric acid and extracted with ethyl acetate. After washing with water and a saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. Then, the obtained crude crystals were washed with n-hexane to obtain 2.4 g (yield: 93%) of the desired product. Melting point: 141-142° C.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materiala saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. customThen, the obtained crude crystals
  7. washwere washed with n-hexane

Sources & evidence

ORD record
ord-53a9f08f958d42188f113efe7cbd8054
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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