Acetic Acid → HCID 15457059, compound

HRID 1385937Notes

Reaction equation

HRID 1385937 reaction equation
[Cl:1][C:2]1[C:7]([S:8](Cl)(=O)=O)=[CH:6][C:5]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[C:4]([F:24])[CH:3]=1.II.[C:27](O)(=[O:29])[CH3:28]>>[C:27]([S:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:24])=[C:5]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)[CH:6]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 807IodineHCID 15457058HCID 15457058, compound

Product 1

HCID 15457059HCID 15457059, compoundYield 98%

Procedure

To 50 ml of acetic acid, 3.1 g (7.7 mmol) of 3-(4-chloro-5-chlorosulfonyl-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone, 1.2 g (38 mmol) of red phosphorus and 0.12 g (0.47 mmol) of iodine were added, followed by heating and refluxing for 1 hour. After cooling, insoluble substances were filtered off, and majority of acetic acid was distilled off. Then, the obtained residue was poured into water and extracted with ethyl acetate. After washing with water and a saturated sodium hydrogencarbonate aqueous solution, the organic layer was washed with anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 2.8 g (yield: 98%) of the desired product. Melting point: 91-92° C.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 1 hour
  3. temperatureAfter cooling
  4. filtrationinsoluble substances were filtered off
  5. distillationmajority of acetic acid was distilled off
  6. additionThen, the obtained residue was poured into water
  7. extractionextracted with ethyl acetate
  8. washAfter washing with water
  9. washa saturated sodium hydrogencarbonate aqueous solution, the organic layer was washed with anhydrous magnesium sulfate
  10. distillationEthyl acetate was distilled off under reduced pressure
  11. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-471c084aeabe42f9941d4090f840d86f
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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