반응 #48461

반응 방정식

2-bromopropanoic acid

carbon disulfide

1-butanethiol

hydrochloric acid

sodium hydroxide

→

title compound

수율 62.2%

2-{[(butylsulfanyl)carbonothioyl]sulfanyl}propanoic Acid

수율 62.2%

용매

Acetone

water

반응 조건

후처리

1. 1
   workup.WAITwas continued for 15 min
2. 2
   workup.STIRRINGThe reaction was stirred overnight
3. 3
   기타The acetone was removed under reduced pressure
4. 4
   추출the remaining mixture was extracted with ether (400 mL)
5. 5
   세척The extract was washed with water (2×100 mL), saturated sodium chloride solution (200 mL)
6. 6
   건조dried (sodium sulfate)
7. 7
   기타evaporated
8. 8
   기타The oily residue was crystallized by the addition of ice (500 g)
9. 9
   여과the crystals were collected by filtration
10. 10
    세척washed with water (5×100 mL)
11. 11
    기타dried in a vacuum oven at room temperature
12. 12
    workup.DISSOLUTIONThe resulting impure product was redissolved in ether (400 mL)
13. 13
    추출extracted with saturated sodium bicarbonate (5×150 mL)
14. 14
    추출extracted with ether (400 mL)
15. 15
    추출The organic extract
16. 16
    세척was washed with saturated sodium chloride (200 mL)
17. 17
    건조dried (sodium sulfate)
18. 18
    기타evaporated under reduced pressure
19. 19
    기타The residue was crystallized by the addition of ice (500 g)
20. 20
    기타the solid was collected
21. 21
    세척washed with water (5×1 50 mL)
22. 22
    기타dried in a vacuum oven

실험 절차

Acetone (700 mL) and tetrapropylammonium bromide (5.58 g, 21.0 mmol) were added with stirring to a solution of sodium hydroxide (10.5 g, 0.263 mol) in water (36 mL), followed by 1-butanethiol (23.7 g, 0.263 mol). After 20 min, carbon disulfide (17 mL, 21.7 g, 0.285 mol) was added and stirring was continued for 15 min, after which 2-bromopropanoic acid (40.14 g, 0.263 mol) was added. The reaction was stirred overnight, then acidified to pH<1 with 2 M hydrochloric acid (100 mL). The acetone was removed under reduced pressure and the remaining mixture was extracted with ether (400 mL). The extract was washed with water (2×100 mL), saturated sodium chloride solution (200 mL), dried (sodium sulfate), and evaporated. The oily residue was crystallized by the addition of ice (500 g), the crystals were collected by filtration and washed with water (5×100 mL) and then dried in a vacuum oven at room temperature. The resulting impure product was redissolved in ether (400 mL) and extracted with saturated sodium bicarbonate (5×150 mL). The combined aqueous extracts were acidified to pH<1 with concentrated hydrochloric acid and extracted with ether (400 mL). The organic extract was washed with saturated sodium chloride (200 mL), dried (sodium sulfate), and evaporated under reduced pressure. The residue was crystallized by the addition of ice (500 g) and the solid was collected and washed with water (5×1 50 mL), then dried in a vacuum oven to give the title compound (15, R3=C4H9) as a yellow solid (39.0 g, 62%).

출처