Reaktion #78817

Reaktionsgleichung

2-chloro-6-methoxy-4-phenylamino-quinazoline

N-methyl-(4-aminophenyl)-methanesulfonamide

→

N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide

Lösungsmittel

methanol

isopentylalcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe warm reaction mixture
2. 2
   Sonstigethe hydrochloride salt, which is crystallizing
3. 3
   Temperaturon cooling
4. 4
   Filtrationis filtered off
5. 5
   workup.DISSOLUTIONThe crude product is redissolved in ethylacetate
6. 6
   Extraktionaqueous sodium carbonate solution and extracted with ethylacetate
7. 7
   SonstigeThe organic extracts are dried
8. 8
   Sonstigeevaporated

Vorschrift

A solution of 2-chloro-6-methoxy-4-phenylamino-quinazoline (1.15 g) and N-methyl-(4-aminophenyl)-methanesulfonamide (prepared as described in Tetrahedron Letters 1992, 33, 8011) (0.89 g) in 5 mL of isopentylalcohol is stirred under nitrogen at 180° C. for 20 min in a sealed vessel. The warm reaction mixture is diluted with methanol and the hydrochloride salt, which is crystallizing on cooling, is filtered off. The crude product is redissolved in ethylacetate and aqueous sodium carbonate solution and extracted with ethylacetate. The organic extracts are dried and evaporated and the solid residue is titurated with diethylether to give N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide as light yellow crystals melting at 212-215° C.; (Rf (A2) 0.16. Recrystallisation from methanolic hydrogen chloride and diethylether yields N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride as light yellow crystals melting at 264-268° C.; Rf (A2) 0.16, FAB-MS: (M+H)+=450. Analytical data: C23H23N5O3S+HCl.

Quelle