Diethyl isopropylidenemalonate → N-(4-fluorophenyl)-N-isopropyl-2-(1-methylethylidene)-N'-((E)-styrylsulfonyl)malonamide

반응식

[CH3:1][C:2](=[C:4]([C:10]([O:12]CC)=O)[C:5]([O:7]CC)=O)[CH3:3].[CH:15](/[S:23]([NH2:26])(=[O:25])=[O:24])=[CH:16]\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:27][C:28]1[CH:37]=[CH:36][C:31]([NH:32][CH:33]([CH3:35])[CH3:34])=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:37]=[CH:36][C:31]([N:32]([CH:33]([CH3:35])[CH3:34])[C:10](=[O:12])[C:4](=[C:2]([CH3:1])[CH3:3])[C:5]([NH:26][S:23](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:24])=[O:25])=[O:7])=[CH:30][CH:29]=1

참가 물질

반응물 3

HCID 81255Diethyl isopropylidenemalonate

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-

HCID 5357731(1E)-2-Phenylethenesulfonamide

생성물 1

HCID 68511856N-(4-fluorophenyl)-N-isopropyl-2-(1-methylethylidene)-N'-((E)-styrylsulfonyl)malonamide수율 0.6%

실험 절차

Diethyl (1-methylethylidene)malonate (5.00 g) was subjected to hydrolysis in the same manner as in Example 1 (1). The obtained carboxylic acid and trans-β-styrenesulfonamide (953 mg) were condensed in the same manner as in Example 152 (3), and the condensed product was subjected to hydrolysis in the same manner as in Example 1 (3). This and 4-fluoro-N-isopropylaniline (805 mg) were condensed in the same manner as in Example 1 (4) to give a crude product. This was purified by silica gel column chromatography to give the title compound (13 mg) as a white powder.