反应详情

Combine 2-methyl-2-propanethiol sodium salt (2.9 g, 26.3 mmol) and 4-(methylthio)benzaldehyde (2.0 g, 13.2 mmol) with dimehtylformamide (40 mL) in a dry flask then heat at 160° C. for 4 hours. Cooled to room temperature, poured into 3N aqueous hydrochloric acid (400 mL) then extracted with dichloromethane (3×75 mL). The combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate, filtered, and concentrated on a rotary evaporator to yield the crude product (3 g). The crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes to yield 4-mercapto-benzaldehyde (0.7 g): 1H NMR (DMSO-D6, 300.00 MHz): 9.9 (s, 1H), 7.7 (d, 2H), 7.5 (d, 2H). Step 2 6-(4-Formyl-phenylsulfanyl)-nicotinamide

1. extractionthen extracted with dichloromethane (3×75 mL)
2. dry with materialThe combined dichloromethane extracts were dried over sodium chloride/magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated on a rotary evaporator
5. customto yield the crude product (3 g)
6. customThe crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate and hexanes