Hydrochloric Acid → Thiazolidine-2-thione-4-carboxylic acid

HRID 1657457Notes

Reaction equation

HRID 1657457 reaction equation
[OH-].[Na+].O.Cl.[NH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][SH:8].[C:12](=S)=[S:13].Cl>O>[C:9]([CH:6]1[CH2:7][S:8][C:12](=[S:13])[NH:5]1)([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 23462L-Cysteine hydrochloride monohydrate

Product 1

HCID 3034757Thiazolidine-2-thione-4-carboxylic acidYield 26.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (40 g, 1.0 mol), cysteine hydrochloride hydrate (50 g, 0.285 mol) and carbon disulfide (30 g, 0.4 mol) were added in that order to 200 ml water at room temperature. This mixture was stirred for 24 hours. At the end of this period, the reaction mixture was acidified to pH 6 with hydrochloric acid and evaporated to yield a yellow foam. Trituration of this foam with concentrated hydrochloric acid caused crystallization to occur. The white solid thus obtained was recrystallized from 6 N hydrochloric acid to yield 12.2 g (21.2%) of 4-carboxythiazolidine-2-thione, m.p. 183°-184°C with decomposition.

Workup

  1. customevaporated
  2. customto yield a yellow foam
  3. customcrystallization
  4. customThe white solid thus obtained
  5. customwas recrystallized from 6 N hydrochloric acid

Sources & evidence

ORD record
ord-ef0e4a1c4bef478baa1660261fe3f692
Source dataset
uspto-grants-1976_06
Patent number
US03960881

Reaction notes

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