Neryl chloride → 2-[(3,7-Dimethyl-2,6(Z)-octadienyl)-thio]-1H-1,3-benzimidazole
反応式
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].O.[CH2:14](Cl)/[CH:15]=[C:16](\[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])/[CH3:17]>CO>[CH3:17]/[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:15]/[CH2:14][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1参加物
5
実験手順
To a solution of 2-mercaptobenzimidazole (5.1 g, 34 mmol) and 2N NaOH/H2O (pH 11) in methanol (100 mL) was added neryl chloride (5.85 g, 34 mmol). The reaction mixture was stirred at ambient temperature for 16 hours, evaporated in vacuo, dissolved in CH2Cl2, washed with saturated NaHCO3 and brine, and dried over Na2SO4. Evaporation of the solvent gave an oil which was flash chromatographed (Merck Kieselgel, 5% MeOH/CH2Cl2) to give the title compound which was crystallized from Et2O/pentane to give a white solid (3.4 g, 35%). m.p. 98°-101° C. NMR (CDCl3)δ7.35(m 4H) 5.25(m 2H) 4.0(d,J=6 Hz,2H), 2.05(m,4H), 1.68(s,3H), 1.62(s,3H), 1.60(s,3H).