m-Chloroperbenzoic acid → 1-Oxido-2-[(2,4,6-trimethylphenyl)methylsulfinyl]pyridin-1-ium

HRID 1829738Notes

Reaction equation

HRID 1829738 reaction equation
[CH3:1][C:2]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:3]=1[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[O-:12].ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:3]=1[CH2:4][S:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[O-:12])=[O:27]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 220547812-(2,4,6-trimethylphenylmethylthio)pyridine N-oxide

Product 1

HCID 5010801-Oxido-2-[(2,4,6-trimethylphenyl)methylsulfinyl]pyridin-1-ium

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 7.8 g (0.03 mole) of 2-(2,4,6-trimethylbenzylthio)-pyridine-N-oxide in 50 ml of chloroform were added, with stirring at less than 10° C., a mixture of 6 g (0.03 mole) of metachloroperbenzoic acid (85%) in 100 ml of chloroform. The mixture was stirred overnight at room temperature. The mixture was then washed with saturated sodium bicarbonate solution, the chloroform layer was separated and dried over sodium sulfate. The sodium sulfate was filtered off and the chloroform solution evaporated to leave a residue, which was crystallized from ethanol. The product was filtered off, and air-dried, melting point 164–166° C., yield 7.2 g. C, H, N, calculated for C15H17NO2S: % C=65.43, % H=6.22; % N=5.09. Found: % C=66.22; % H=6.63; % N=5.13.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred overnight at room temperature
  3. washThe mixture was then washed with saturated sodium bicarbonate solution
  4. customthe chloroform layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationThe sodium sulfate was filtered off
  7. customthe chloroform solution evaporated
  8. customto leave a residue, which
  9. customwas crystallized from ethanol
  10. filtrationThe product was filtered off
  11. customair-dried

Sources & evidence

ORD record
ord-f733b0d0640e46a393e35386fec52994
Source dataset
uspto-grants-2006_06
Patent number
US07064139B2

Reaction notes

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