Carbon Disulfide → 2-((Butylsulfanyl)carbonothioyl)sulfanyl)propanoic acid

Dodecanethiol (2.50 g, 12.5 mmol), acetone (40 mL), and tetrapropylammonium bromide (0.27 g, 0.10 mmol) were added to a solution of sodium hydroxide (0.50 g, 12.5 mmol) in water (5 mL). The resulting solution was cooled in an ice bath and treated with carbon disulfide (0.75 mL, 0.95 g, 12.5 mmol). After 20 min, 2-bromopropanoic acid (1.91 g, 12.5 mmol) was added and the mixture was stirred at ambient temperature for 12 h. The solution was evaporated to ¼ volume and slowly acidified with 2 M hydrochloric acid (50 mL), then further diluted with water (150 mL). The resulting solid was collected and recrystallised from ether/light petroleum to give the title compound (15, R3=C12H25) as yellow crystals (3.33 g, 76%).

1. temperatureThe resulting solution was cooled in an ice bath
2. customThe solution was evaporated
3. additionfurther diluted with water (150 mL)
4. customThe resulting solid was collected
5. customrecrystallised from ether/light petroleum

ORD-Eintrag

ord-cbdd9b4994364bda8b1573b9e3f599bd

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745553B2