Water → 3-[(Pyridin-2-yl)disulfanyl]propanoic acid

HRID 1759302Notes

Reaction equation

HRID 1759302 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]Cl.[SH:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].O.[OH-].[Na+]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 65143-Mercaptopropionic AcidHCID 14798Sodium HydroxideHCID 135348172-(Chlorosulfanyl)pyridine

Product 1

HCID 118060883-[(Pyridin-2-yl)disulfanyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.4 g of 2-pyridine sulfenyl chloride are dissolved in 40 ml of methylene chloride, and a solution of 1.75 g of 3-mercaptopropionic acid in 10 ml of methylene chloride is added slowly, whilst stirring and cooling with an ice bath. When the addition is complete, the mixture is stirred at ambient temperature for 15 hours. 50 ml of water are added and the pH is brought to 4.5 by adding 1 N sodium hydroxide solution. The organic phase is separated off and dried over sodium sulphate and the solvent is evaporated off to dryness. An oily product remains and this crystallises (1.8 g). It is purified by dissolution in 16.8 ml of a 0.5 M aqueous solution of sodium bicarbonate. Activated charcoal is added, the solution is filtered and the expected product is then precipitated by adding concentrated acetic acid (0.5 ml) so as to bring the pH to between 3 and 3.5. The precipitate is filtered off and dried under high vacuum and a solid (1.3 g), melting point (capillary method): 62°-64° C., is obtained.

Workup

  1. temperaturecooling with an ice bath
  2. additionWhen the addition
  3. stirringthe mixture is stirred at ambient temperature for 15 hours
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is evaporated off to dryness
  7. customthis crystallises (1.8 g)
  8. customIt is purified by dissolution in 16.8 ml of a 0.5 M aqueous solution of sodium bicarbonate
  9. additionActivated charcoal is added
  10. filtrationthe solution is filtered
  11. customthe expected product is then precipitated
  12. additionby adding concentrated acetic acid (0.5 ml) so as
  13. filtrationThe precipitate is filtered off
  14. customdried under high vacuum
  15. custom62°-64° C., is obtained

Sources & evidence

ORD record
ord-0e3677b15ab2496889186bdbc21eb3a1
Source dataset
uspto-grants-1982_07
Patent number
US04340535

Reaction notes

Loading…