Dimethyl Sulfoxide → HCID 15457043, compound

HRID 1385918Notes

Reaction equation

HRID 1385918 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([C:12]2[C:13](=[O:28])[C:14](C(OCC)=O)=[C:15]([C:19]([F:22])([F:21])[F:20])[N:16]([CH3:18])[CH:17]=2)=[C:4]([F:29])[CH:3]=1.[Cl-].[Na+].CS(C)=O>O>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:6][C:5]([C:12]2[C:13](=[O:28])[CH:14]=[C:15]([C:19]([F:20])([F:21])[F:22])[N:16]([CH3:18])[CH:17]=2)=[C:4]([F:29])[CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 15457042HCID 15457042, compound

Product 1

HCID 15457043HCID 15457043, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
190 °C

Procedure

0.7 g (1.6 mmol) of 5-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3-ethoxycarbonyl-1-methyl-2-trifluoromethyl-4(1H)-pyridone, 0.15 g (2.5 mmol) of sodium chloride and 0.1 ml of water were added to 5 ml of dimethylsulfoxide, followed by stirring at 190° C. for 3 hours. After cooling, this reaction solution was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and then, the obtained residue was purified by silica gel column chromatography to obtain 0.10 g (yield: 17%) of the desired product. Melting point: 150-151° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f2f49513e2d471ca5932d31804b0a18
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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