Reaktion #1169451

Reaktionsgleichung

hydrochloric acid

4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

2-mercaptoethanol

sodium hydride

→

4-tert-butyl-N-{6-(2-hydroxyethylthio)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

Ausbeute 69.5%

Lösungsmittel

dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture is reacted under argon atmosphere at 70° C. for two hours, at 100° C. for three hours
2. 2
   Sonstigefurther reacted at 130° C. for two hours
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe ethyl acetate layer is washed
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto remove the solvent
8. 8
   SonstigeThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=70:1)
9. 9
   Sonstigerecrystallized from ethyl acetate/n-hexane

Vorschrift

To a solution of 2-mercaptoethanol (1.31 g) in dimethylacetamide (15 ml) is added sodium hydride (62.3% dispersion-type, 520 mg) under argon atmosphere. Five minutes later, to the mixture is added 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (1.5 g), and the mixture is reacted under argon atmosphere at 70° C. for two hours, at 100° C. for three hours, and further reacted at 130° C. for two hours. The reaction solution is treated with hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=70:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-{6-(2-hydroxyethylthio)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (1.14 g) as crystals.

Quelle