(+-)-2-Mercaptopropionic acid → HCID 23686688, compound

HRID 1758086Notes

Reaction equation

HRID 1758086 reaction equation
C[O-].[Na+:3].Cl.[N:5]1[CH:10]=[CH:9][C:8]([CH2:11]Cl)=[CH:7][CH:6]=1.[SH:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16]>C(O)C>[N:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:13][CH:14]([CH3:18])[C:15]([O-:17])=[O:16])=[CH:7][CH:6]=1.[Na+:3]

Participants

5

Reactant 3

HCID 62326(+-)-2-Mercaptopropionic acidHCID 745704-(Chloromethyl)pyridinium chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 23686688HCID 23686688, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Sodium methoxide (5.1 g., 94 mmoles) was dissolved in 50 ml. of absolute ethanol and cooled in an ice bath. A slurry of 4-picolyl chloride hydrochloride (5.0 g., 30.4 mmoles) in 45 ml. of ethanol was added and the chilled reaction mixture stirred for approximately 10 minutes. Finally, 2-mercaptopropionic acid (3.23 g., 30.4 mmoles) dissolved in 5 ml. of ethanol was added over a 10 minute period. The mixture was allowed to warm to room temperature and stirred overnight (approximately 16 hours). The reaction was filtered through filter aid to remove salts, carbon treated and concentrated to crude sodium 2-(4-picolylthio)propionate (approximately 7 g. of oil used directly in the next step).

Workup

  1. customthe chilled reaction mixture
  2. stirringstirred overnight (approximately 16 hours)
  3. filtrationThe reaction was filtered
  4. filtrationthrough filter aid
  5. customto remove salts, carbon
  6. additiontreated
  7. concentrationconcentrated to crude sodium 2-(4-picolylthio)propionate (approximately 7 g

Sources & evidence

ORD record
ord-bf272d2959f342a89daae44cc9384ed3
Source dataset
uspto-grants-1983_02
Patent number
US04371696

Reaction notes

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