m-Chloroperbenzoic acid → HCID 12807840, compound

HRID 325623Notes

Reaction equation

HRID 325623 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]([CH2:13][S:14][CH3:15])=[CH:3]1.ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]([CH2:13][S:14]([CH3:15])=[O:24])=[CH:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12807839HCID 12807839, compound

Product 1

HCID 12807840HCID 12807840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the above 1-methyl-3-methylthiomethyl-4-quinolone (4.86 g.) in dichloromethane (220 ml.) at -20° was added a solution of 3-chloroperbenzoic acid (85%, 4.86 g.) in dichloromethane (220 ml.) during 1 hour. The solution was allowed to warm to room temperature and 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. The product was crystallised from acetone to give the novel 1-methyl-3-methylsulphinylmethyl-4-quinolone, m.p. 93°-95°.

Workup

  1. extractionextracted 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. customThe product was crystallised from acetone

Sources & evidence

ORD record
ord-4f0ff9194cb646018e9b14d89d93f3fb
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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