反应详情

To a suspension of sodium hydride (NaH) (0.69 g, 30 mmol) in dimethylformamide (DMF) (100 mL) was added 2-mercaptobenzimidazole (4.5 g, 10 mmol) in DMF (20 mL) at 0° C. under N2. To the resultant solution was added geranyl chloride (5.16 g, 10 mmol) over 30 minutes. The reaction was stirred for five hours at ambient temperature under N2 then treated with 2N NaOH and extracted with diethyl ether (Et2O). The Et2O extract was washed with saturated NaCl, concentrated in vacuo, dissolved in methylene chloride, and dried over Na2SO4. Recrystallization from Et2O gave white crystalline 2-[(3,7-dimethyl-2,6(E)-octadienyl)-thio]-1H-1,3-benzimidazole (3.15 g, 36.6%). m.p. 98°-100° C. NMR (CDCl3):δ7.4(m, 2H), 7.1(m, 2H) 5.3(t,J=8 Hz, 1H) 5.0(m 1H) , 3.90(d, J= 10 Hz, 2H , 2.00(m, 4H), 1.65(m, 9H).

1. extractionextracted with diethyl ether (Et2O)
2. extractionThe Et2O extract
3. washwas washed with saturated NaCl
4. concentrationconcentrated in vacuo
5. dissolutiondissolved in methylene chloride
6. dry with materialdried over Na2SO4
7. customRecrystallization from Et2O