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

HRID 329139

Reaction equation

HRID 329139 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[Na].[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([CH2:18]Cl)=[C:13]([CH3:20])[CH:12]=1>C(O)C>[CH3:20][C:13]1[CH:12]=[C:11]([CH3:10])[CH:16]=[C:15]([CH3:17])[C:14]=1[CH2:18][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8]

Participants

5

Reactant 3

HCID 741082,4,6-Trimethylbenzyl chlorideHCID 5360545SodiumHCID 178526253HCID 178526253, compound

Product 1

HCID 220547812-(2,4,6-trimethylphenylmethylthio)pyridine N-oxideYield 88.7%

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) α2 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 induce 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-aab389400d344cb691183917617e1f32
Source dataset
uspto-grants-1977_04
Patent number
US04019893

Linked notes

Loading…