m-Chloroperbenzoic acid → 1-Methyl-3-methylsulphinylmethyl-7-trifluoromethyl-4-quinolone

HRID 325628Notes

Reaction equation

HRID 325628 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[C:5](=[O:16])[C:4]([CH2:17][S:18][CH3:19])=[CH:3]1.ClC1C=CC=C(C(OO)=[O:28])C=1>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=2)[C:5](=[O:16])[C:4]([CH2:17][S:18]([CH3:19])=[O:28])=[CH:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128078421-Methyl-3-methylthiomethyl-7-trifluoromethyl-4-quinolone

Product 1

HCID 128078431-Methyl-3-methylsulphinylmethyl-7-trifluoromethyl-4-quinolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-methyl-3-methylthiomethyl-7-trifluoromethyl-4-quinolone (6.5 g.) in dichloromethane (150 ml.) at -10° was added a solution of 3-chloroperbenzoic acid (85%, 4.2 g.) in dichloromethane (90 ml.) during 30 minutes. The solution was extracted with saturated aqueous sodium bicarbonate until free of per-acid. The organic phase was dried over anhydrous magnesium sulphate and evaporated to give a solid product. This was crystallised from ethyl acetate:dichloromethane to give the novel 1-methyl-3-methylsulphinylmethyl-7-trifluoromethyl-4-quinolone, m.p. 208°-210°.

Workup

  1. extractionThe solution was extracted with saturated aqueous sodium bicarbonate until free of per-acid
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customevaporated
  4. customto give a solid product
  5. customThis was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-90208ae83c3f4f1798f89d2c41f9da0c
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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