反応 #78817

反応方程式

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

N-methyl-(4-aminophenyl)-methanesulfonamide

→

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

溶媒

methanol

isopentylalcohol

反応条件

後処理

1. 1
   その他The warm reaction mixture
2. 2
   その他the hydrochloride salt, which is crystallizing
3. 3
   温度on cooling
4. 4
   ろ過is filtered off
5. 5
   workup.DISSOLUTIONThe crude product is redissolved in ethylacetate
6. 6
   抽出aqueous sodium carbonate solution and extracted with ethylacetate
7. 7
   その他The organic extracts are dried
8. 8
   その他evaporated

実験手順

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.

出典