Thiophenol → 2-chloro-6-thiophenylpyridine N-oxide

HRID 1488729Notes

Reaction equation

HRID 1488729 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N+:3]=1[O-:9].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=CC=1.[OH-].[Na+]>CS(C)=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:13]2[S:16][CH:10]=[CH:15][CH:14]=2)[N+:3]=1[O-:9]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 8176732,6-Dichloropyridine N-Oxide

Product 1

HCID 867487302-chloro-6-thiophenylpyridine N-oxide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 1.64 g (0.010 moles) of 2,6-dichloropyridine N-oxide and 1.11 g (99%) (0.010 moles) of thiophenol was reacted with 0.400 g (0.010 moles) of ground sodium hydroxide of 16.4 ml of DMSO at 80° C. for 5 hours to give 2-chloro-6-thiophenylpyridine N-oxide. It was reacted with 1.20 g (0.030 moles) of ground sodium hydroxide at 80° C. for 2.5 hours to give 1-hydroxy-6-thiophenylpyridine-2(1H)-one. After cooling, it was added 148 ml of water and was adjusted with 6N HCl to pH 3. The precipitate was filtered, washed with water and washed with hexanes to give 1.64 g (75%). It was recrystallized from ethanol: mp 180°-181° C.

Sources & evidence

ORD record
ord-d3546c304ec74543916c2c1ae1a57f55
Source dataset
uspto-grants-1997_10
Patent number
US05675013

Reaction notes

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