반응 #78817

반응 방정식

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

N-methyl-(4-aminophenyl)-methanesulfonamide

→

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

용매

methanol

isopentylalcohol

반응 조건

후처리

1. 1
   기타The warm reaction mixture
2. 2
   기타the hydrochloride salt, which is crystallizing
3. 3
   온도on cooling
4. 4
   여과is filtered off
5. 5
   workup.DISSOLUTIONThe crude product is redissolved in ethylacetate
6. 6
   추출aqueous sodium carbonate solution and extracted with ethylacetate
7. 7
   기타The organic extracts are dried
8. 8
   기타evaporated

실험 절차

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.

출처