Sodium Hydroxide → HCID 178443467, compound

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.[OH-].[Na+].[CH2:14](Cl)/[CH:15]=[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])\[CH3:17]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([S:9][CH2:14]/[CH:15]=[C:16](\[CH3:17])/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[N:8][C:4]=2[CH:3]=1

Participants

Procedure

To a solution of the 5-chloro-2-mercaptobenzimidazole (0.665 g, 3.6 mmol) in methanol (10 mL) and 2N NaOH (7 mmol) was added geranyl chloride (0.775 g, 4.5 mmol). The reaction mixture was stirred at ambient temperature for 24 hours, evaporated in vacuo, dissolved in CH2Cl2, washed with water, and dried over Na2SO4. Evaporation and flash chromatography (Merck Kieselgel, CH2Cl2) gave an oil which was crystallized with pentane to yield a white solid of the title compound (270 mg). m.p. 102°-104° C. NMR (CDCl3)δ7.45-7.0(m,3H), 5.37(t, J=7 Hz,1H), 5.03(t,J=7Hz, 1H), 3.93(d,J=8 Hz,2H), 2.02(m,4H), 1.67(s,3H), 1.66(s,3H), 1.58(s,3H).