Methanol → 1-[5-(2-Chlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone

反応式

C[O-].[Na+].CO.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[SH:13].Cl[C:15]1[S:19][C:18]([C:20](=[O:22])[CH3:21])=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24]>>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:15]1[S:19][C:18]([C:20](=[O:22])[CH3:21])=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24]

参加物

反応物 4

HCID 887Methanol

HCID 80599o-Chlorothiophenol

HCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one

HCID 10942334Sodium Methoxide

生成物 1

HCID 469318591-[5-(2-Chlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone収率 52.6%

実験手順

To a 0.1 M stock solution of sodium methoxide in anhydrous methanol (11 mL, 1.1 mmol) was added the 2-chlorobenzenethiol (0.144 g, 1 mmol) and the resulting mixture stirred at ambient temperature for 15 minutes. 1-(5-Chloro-4-nitro-2-thienyl)ethanone (206 mg, 1 mmol) was added and the mixture was stirred at ambient temperature for 2 hours. After this time the reaction was quenched by the addition of water (15 mL) and the resulting precipitate was collected by filtration, washed with water (10 mL) and dried in vacuo at 40° C. overnight. The solid was then crystallized from acetonitrile to afford the title compound as a dark orange solid (165 mg, 52.6% yield). 1H NMR (300 MHz, CDCl3) δ: 8.09 (1H, s), 7.77 (1H, ddd, J=7.58, 1.58, 0.36 Hz), 7.40-7.67 (3H, m), 2.49 (3H, s).