Reaktion #430541

Reaktionsgleichung

5-dimethylamino-1-naphthalenesulphonyl chloride

3-amino-6-chloropyridazine

→

5-(dimethylamino)-N-(6-chloro-3-pyridazinyl)-1-naphthalenesulphonamide

Ausbeute 32.5%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeVolatile material was removed by evaporation and dichloromethane (50 ml)
2. 2
   workup.ADDITIONwas added
3. 3
   SonstigeInsoluble material was removed by filtration
4. 4
   Einengenthe filtrate was concentrated by evaporation
5. 5
   SonstigeThe residue was purified by flash chromatography
6. 6
   Wascheneluting with ethyl acetate/hexane (1:1 v/v)
7. 7
   Sonstigethe resulting foam was crystallised from ether

Vorschrift

A solution of 5-dimethylamino-1-naphthalenesulphonyl chloride (3.98 g), 3-amino-6-chloropyridazine (1.91 g) and 4-dimethylaminopyridine (100 mg) in pyridine (25 ml) was heated at 85° C for 18 hours. Volatile material was removed by evaporation and dichloromethane (50 ml) was added. Insoluble material was removed by filtration and the filtrate was concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), and the resulting foam was crystallised from ether to give 5-(dimethylamino)-N-(6-chloro-3-pyridazinyl)-1-naphthalenesulphonamide (1.74 g), m.p. 153°-154° C.; mass spectrum (positive chemical ionisation ((+)ve CI)): 363 (M+H)+.

Quelle