Reaktion #430554

Reaktionsgleichung

5-dimethylamino-1-naphthalenesulphonyl chloride

2-Amino-5-bromo-6-chloropyrazine

sodium hydride

hydrochloric acid

hydrogen

→

5-dimethylamino-N-(5-bromo-6-chloro-2-pyrazinyl)-1-naphthalenesulphonamide

Ausbeute 52.1%

Lösungsmittel

dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with ethyl acetate (2×25 ml)
2. 2
   Trocknenthe extracts were dried (MgSO4)
3. 3
   SonstigeVolatile material was removed by evaporation
4. 4
   Sonstigethe residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column

Vorschrift

2-Amino-5-bromo-6-chloropyrazine (0.417 g) was added to a stirred suspension of sodium hydride (oil-free; 0.24 g) in dry dimethoxyethane (20 ml). When evolution of hydrogen ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.594 g) was added. The mixture was stirred for 24 hours and then water (25 ml) and 2M hydrochloric acid (2 ml) were added. The mixture was extracted with ethyl acetate (2×25 ml) and the extracts were dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by elution with ethyl acetate/hexane (1:3 v/v) through a silica gel Mega Bond Elut column to give 5-dimethylamino-N-(5-bromo-6-chloro-2-pyrazinyl)-1-naphthalenesulphonamide (0.46 g), m.p. 180°-182° C. (after trituration with ether); mass spectrum (+ve FAB, methanol/NBA): 442 (M+).

Quelle