Hydrochloric Acid → 2-Oxo-1,3-thiazolidine-5-carboxylic acid

HRID 487976Notes

Reaction equation

HRID 487976 reaction equation
[OH-:1].[Na+].Cl.[NH2:4][CH2:5][CH:6]([S:10][C:11](CC1C=CC=CC=1)=S)[C:7]([OH:9])=[O:8].Cl>C(O)C>[O:1]=[C:11]1[NH:4][CH2:5][CH:6]([C:7]([OH:9])=[O:8])[S:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86747702HCID 86747702, compound

Product 1

HCID 189610442-Oxo-1,3-thiazolidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.0 ml of a 1 N aqueous solution of sodium hydroxide were added to a suspension of 1.2 g of 3-amino-2-(benzylthiocarbonylthio)propionic acid hydrochloride in 35 ml of ethanol, and the resulting mixture was stirred at room temperature for 30 minutes, after which 12.0 ml of 1 N aqueous hydrochloric acid were added, whilst ice-cooling. The solvent was then removed by distillation under reduced pressure, the resulting residue was dissolved in diethyl ether and the solution was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 0.50 g of a colorless powder. This powder was recrystallized from ethyl acetate, to give 0.25 g of the title compound as colorless columnar crystals, melting at 148°-150° C.

Workup

  1. temperaturecooling
  2. customThe solvent was then removed by distillation under reduced pressure
  3. dissolutionthe resulting residue was dissolved in diethyl ether
  4. dry with materialthe solution was dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-3e5df2a8b7094439bdbf5641b1aaf4dc
Source dataset
uspto-grants-1994_03
Patent number
US05298516

Reaction notes

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