Stannous chloride dihydrate → 4-(benzylsulfanyl)aniline

反応式

O.O.[Sn](Cl)Cl.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([O-])=O>C(O)C.C(OCC)(=O)C>[CH2:16]([S:15][C:12]1[CH:11]=[CH:10][C:9]([NH2:6])=[CH:14][CH:13]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

反応条件

温度: 70 °C

実験手順

Tin (II) chloride dihydrate (444 mg) was added to a stirred solution of benzyl 4-nitrophenyl sulfide (A, 704 mg) in ethanol (20 mL). The mixture was stirred at 70° C. for 2 hr under nitrogen, allowed to cool down and then poured into ice. The pH was made slightly basic (pH 7-8). The mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (565 mg) as a brown oil: 1H NMR (400 MHz, CDCl3) δ 3.59 (br s, 2H), 3.93 (s, 2H), 6.54-6.57 (m, 2H), and 7.11-7.26 (m, 7H).