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

HRID 485051Notes

Reaction equation

HRID 485051 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-000599df8e7c4607a90cedfc72a097b2
Source dataset
uspto-grants-1985_08
Patent number
US04535084

Reaction notes

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