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

HRID 1488729

Reaktionsgleichung

Reaktionsgleichung von HRID 1488729
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 867487302-chloro-6-thiophenylpyridine N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-d3546c304ec74543916c2c1ae1a57f55
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05675013

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