Thiocarbonic acid, anhydrosulphide with methyl thiohypochlorite → 2-(2-Pyridyldithio)ethanol

Temperature

0 °C

To a solution of methoxycarbonyl sulfenyl chloride (10 mL, 110 mmol), in dichloromethane (100 mL), cooled to 0° C., was added mercaptoethanol (7.6 mL, 110 mmol), dropwise. The reaction mixture was allowed to stir at 0° C. for 30 min At this point, a solution of 2-mercaptopyridine (12.2 g, 110 mmol) in dichloromethane (160 mL) was added. The solution was allowed to react at 0° C. for 1 hr and then was allowed to warm to RT for another 1 hr. Solid product was observed to have fallen out of solution. TLC (1:1 Pet Ether/EtOAc) showed that significant product had been formed. The reaction mixture was concentrated to a volume of 125 mL. The mixture was filtered through a Buchner funnel. The filter cake was washed with dichloromethane and then dried under vacuum overnight to afford 2-(2-(Pyridin-2-yl)disulfanyl)ethanol (23.6 g), as the HCl salt.

1. customto react at 0° C. for 1 hr
2. temperatureto warm to RT for another 1 hr
3. customhad been formed
4. concentrationThe reaction mixture was concentrated to a volume of 125 mL
5. filtrationThe mixture was filtered through a Buchner funnel
6. washThe filter cake was washed with dichloromethane
7. customdried under vacuum overnight

ORD record

ord-b78b9e0d71064041bb9aa647d287af37

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299266B2