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

HRID 1829729Notes

Reaction equation

HRID 1829729 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-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

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

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe filter cake is washed thoroughly with water and finally with 40 ml of acetone
  4. customVacuum drying of the cake

Sources & evidence

ORD record
ord-67a3611213dc48a9bb743e5d1c3c6580
Source dataset
uspto-grants-2006_06
Patent number
US07064139B2

Reaction notes

Loading…