Sodium methanethiolate → 5-Chloro-2-methylthio-3-pyridinecarbonitrile

5,6-Dichloro-3-pyridinecarbonitrile (1.73 g, 0.01 mol) was dissolved with stirring in dimethyl sulphoxide (25 mL) and sodium methanethiolate (0.77 g, 0.011 mol) added. The reaction mixture was stirred at room temperature for two hours and poured onto ice (100 g). The mixture was extracted with dichloromethane (50 mL), and the organic extract washed with water (100 mL), and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and recrystallisation of the residue from ethyl acetate:hexane gave the desired product (1.3 g, 71%) as a cream solid, MP 147-9° C.

1. additionpoured onto ice (100 g)
2. extractionThe mixture was extracted with dichloromethane (50 mL)
3. extractionthe organic extract
4. washwashed with water (100 mL), and brine
5. dry with materialdried over anhydrous sodium sulphate
6. customEvaporation of the solvent
7. customunder reduced pressure and recrystallisation of the residue from ethyl acetate

ORD record

ord-726385f03c9446b5ae77352515a07821

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133294