Hydrochloric Acid → 3-(Acetylthio)-2-[(acetylthio)methyl]propanoic acid

HRID 1252826Notes

Reaction equation

HRID 1252826 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].Br[CH2:6][CH:7]([CH2:11]Br)[C:8]([OH:10])=[O:9].Cl>[OH-].[K+]>[C:1]([S:3][CH2:6][CH:7]([CH2:11][S:3][C:1](=[O:4])[CH3:2])[C:8]([OH:10])=[O:9])(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3189153-Bromo-2-(bromomethyl)propionic acidHCID 178418634HCID 178418634, compound

Product 1

HCID 131455313-(Acetylthio)-2-[(acetylthio)methyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of 3.36 g (40 mmoles) of thioacetic acid in 40 ml of N-potassium hydroxide is added dropwise to a solution of 2-bromomethyl-3-bromopropanoic acid in 1.0N potassium hydroxide (20 ml). The mixture is stirred at room temperature overnight, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer is dried and concentrated in vacuo. The residue is converted into a dicyclohexylammonium salt (m.p. 116°-118°) and the salt converted back into the free acid, 2-(acetylthiomethyl)-3-(acetylthio)propanoic acid, by distribution between ethyl acetate and 10% potassium bisulfate.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0094c45a9b94187bcd71483166700ed
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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