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

HRID 1595122Notes

Reaction equation

HRID 1595122 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].COC(SCl)=O.[SH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>C(Cl)Cl>[CH:18]1[CH:19]=[C:14]([S:13][S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[N:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 123417Thiocarbonic acid, anhydrosulphide with methyl thiohypochloriteHCID 178418616HCID 178418616, compound

Product 1

HCID 118060883-[(Pyridin-2-yl)disulfanyl]propanoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

5.00 g (52.2 mmol) of 3-mercaptopropanoic acid (Aldrich Chemical Co., Milwaukee, Wis.) in 75 ml of dry methylene chloride was added to a solution of 5.96 g (52.2 mmol) of methoxycarbonylsulfenyl chloride (Fluka Chemika, Long Island, N.Y.) in 150 ml of dry methylene chloride. The mixture was stirred at 15-25° C. for 90 minutes and then concentrated. The residue was redissolved in 150 ml of dry methylene chloride and dropwise treated with 5.80 g (52.2 mmol) of 2-mercaptopyridine (Aldrich Chemical Co.) in 75 ml of dry methylene chloride. The mixture was stirred at 15-25° C. for 18 hours and concentrated to afford 11.2 g of the product as a pale yellow oil (99%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in 150 ml of dry methylene chloride
  3. stirringThe mixture was stirred at 15-25° C. for 18 hours
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-35b65619d10b4f80bc09d69b9b9b1cbb
Source dataset
uspto-grants-2001_09
Patent number
US06287536B1

Reaction notes

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