Sodium → 2-(2,4,6-trimethylphenylmethylthio)pyridine N-oxide

HRID 1657331Notes

Reaction equation

HRID 1657331 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[Na].Cl[CH2:11][C:12]1[CH:20]=[C:18]([CH3:19])[CH:17]=[C:15]([CH3:16])[C:13]=1[CH3:14]>C(O)C>[CH3:11][C:12]1[CH:20]=[C:18]([CH3:19])[CH:17]=[C:15]([CH3:16])[C:13]=1[CH2:14][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 223236781-(Chloromethyl)-2,3,5-trimethylbenzeneHCID 178526253HCID 178526253, compound

Product 1

HCID 220547812-(2,4,6-trimethylphenylmethylthio)pyridine N-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 17 gms (0.05 mole) 2-mercaptopyridine N-oxide, sodium salt (40% aqueous solution) and 8.5 gms (0.05 mole) α 2 chloroisodurene in 50 ml of ethanol is brought to reflux for 15 minutes. The volatiles are removed and the residue extracted with 150 ml of boiling chloroform, filtered and dried over sodium sulfate. Evaporation and trituration of the residue with a few drops of acetone induced crystallization. A yield of 11.5 gms of 2-(2,4,6-trimethylphenylmethylthio)pyridine N-oxide is obtained. Melting point 137° - 138°C. Structure confirmed by IR and NMR.

Workup

  1. temperatureto reflux for 15 minutes
  2. customThe volatiles are removed
  3. extractionthe residue extracted with 150 ml of boiling chloroform
  4. filtrationfiltered
  5. dry with materialdried over sodium sulfate
  6. customEvaporation and trituration of the residue with a few drops of acetone
  7. customcrystallization

Sources & evidence

ORD record
ord-7fa0ddf893044b9ea3298008acafb611
Source dataset
uspto-grants-1976_06
Patent number
US03960542

Reaction notes

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