Water → HCID 18755515, compound

HRID 1838646Notes

Reaction equation

HRID 1838646 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([C:10]2[C:11](=[O:23])[CH2:12][CH2:13][CH2:14][C:15]=2[S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:9])=[CH:6][CH:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[N:3]=1.C(OO)(=[O:30])C.C(OCC)(=O)C.[OH2:39]>C(Cl)Cl>[C:17]1([S:16]([C:15]2[CH2:14][CH2:13][CH2:12][C:11](=[O:23])[C:10]=2[C:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([C:24]([F:25])([F:27])[F:26])=[CH:5][CH:6]=2)=[O:9])(=[O:30])=[O:39])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6585Peracetic AcidHCID 8857Ethyl AcetateHCID 18755535HCID 18755535, compound

Product 1

HCID 18755515HCID 18755515, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.8 g (0.00204 mol) of the 2-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-3-phenylsulfanylcyclohex-2-enone obtained above is dissolved in 30 ml of methylene chloride, and 1.39 ml of peracetic acid (39% in acetic acid, 0.00816 mol) are subsequently added dropwise at a temperature of 25° C. After 4 hours at 25° C., the reaction mixture is poured into ethyl acetate and water, the organic phase is washed with water, dried with sodium sulfate and concentrated, and the residue is triturated with a small amount of hexane and ethyl acetate. Filtration gives 0.72 g (84% of theory) of 3-benzenesulfonyl-2-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)cyclohex-2-enone in the form of white crystals of melting point 165-167° C. 1H-NMR (CDCl3): 2.30, m, 2H; 2.55, t (J, 7 Hz), 2H; 2.71, m, 2H; 3.05, s, 3H; 7.40-7.80, m, 4H; 7.80-8.05 ppm, m, 3H.

Workup

  1. washthe organic phase is washed with water
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated
  4. customthe residue is triturated with a small amount of hexane and ethyl acetate
  5. filtrationFiltration

Sources & evidence

ORD record
ord-d0feed1da3a04d3ab8436dc6dd009e4d
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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