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

HRID 21695

Reaction equation

HRID 21695 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-dd733e1a9b8e43559d9f6fc67ca8840f
Source dataset
uspto-grants-1995_06
Patent number
US05424435

Linked notes

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