Chlorosulfonic acid → HCID 15457058, compound

HRID 1385936Notes

Reaction equation

HRID 1385936 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)=[C:4]([F:20])[CH:3]=1.[Cl:21][S:22](O)(=[O:24])=[O:23]>>[Cl:1][C:2]1[C:7]([S:22]([Cl:21])(=[O:24])=[O:23])=[CH:6][C:5]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:16])([F:17])[F:15])=[CH:12][CH:13]=2)=[C:4]([F:20])[CH:3]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 15457048HCID 15457048, compound

Product 1

HCID 15457058HCID 15457058, compoundYield 86%

Conditions

Temperature
100 °C

Procedure

2.9 g (9.5 mmol) of 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 70 g of chlorosulfonic acid, followed by heating and stirring at 100° C. for 5 hours. After cooling, the mixture was gradually dropwise added to ice water, followed by extraction with ethyl acetate. After washing with water and a saturated sodium hydrogencarbonate 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 3.3 g (yield: 86%) of the desired product. Melting point: 77-78° C.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washAfter washing with water
  5. dry with materiala saturated sodium hydrogencarbonate aqueous solution, the organic layer was dried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customThen, the obtained crude crystals
  8. washwere washed with n-hexane

Sources & evidence

ORD record
ord-ee14aecdb8b344ffb33838c1be1cc482
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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