2,6-Dichlorobenzyl chloride → 2-(2,6-dichlorophenylmethylthio)pyridine N-oxide

HRID 329140

Reaction equation

HRID 329140 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[Na].[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13]Cl>C(O)C>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8]

Participants

5

Reactant 3

HCID 748322,6-Dichlorobenzyl chlorideHCID 5360545SodiumHCID 178526253HCID 178526253, compound

Product 1

HCID 124315032-(2,6-dichlorophenylmethylthio)pyridine N-oxideYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 37 gms (0.1 mole) 2-mercaptopyridine N-oxide, sodium salt (40% aqueous solution) and 19.5 gms (0.1 mole) 2,6-dichlorobenzylchloride in 200 ml of ethanol is warmed to 65° - 70° for thirty minutes, cooled and filtered. The filter cake is washed thoroughly with water and finally with 40 ml of acetone. The dry cake (25.3 gms) represents a 92% yield of 2-(2,6-dichlorophenylmethylthio)pyridine N-oxide. Melting point 240° - 241° C. Structure confirmed by IR and NMR.

Workup

  1. temperatureis warmed to 65° - 70° for thirty minutes
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe filter cake is washed thoroughly with water and finally with 40 ml of acetone

Sources & evidence

ORD record
ord-3738219504b04e26821a1b48bc817ea8
Source dataset
uspto-grants-1977_04
Patent number
US04019893

Linked notes

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