Carbon Disulfide → (S)-4-Phenylthiazolidine-2-thione

HRID 1167698Notes

Reaction equation

HRID 1167698 reaction equation
[C:1]1([C@@H:7]([CH2:9]O)[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11](=[S:13])=[S:12]>[OH-].[K+].O>[C:1]1([C@H:7]2[CH2:9][S:13][C:11](=[S:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 1347972-Amino-2-phenylethan-1-ol

Product 1

HCID 11333042(S)-4-Phenylthiazolidine-2-thioneYield 9%

Reagents, catalysts & solvents 1

HCID 23719240Potassium hydroxide monohydrateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (S)-(+)-2-Phenylglycinol(1.40 g, 10 mmol) in 1N KOH/H2O (10 ml) at room temperature, was added carbon disulfide (3 ml, 50 mmol). The resulting solution was heated by a pre-heated oil-bath (110° C.) to reflux for 20 h after which the reaction mixture was cooled to room temperature and extracted with CH2Cl2 (3×30 ml), dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 1:1 hexane/CH2Cl2 followed by CH2Cl2 as the eluting system (Rf=0.09, CH2Cl2:hexane=7:3) to obtain 4(S)-phenyl-thiazolidine-2-thione (170 mg, 9%).

Workup

  1. temperatureto reflux for 20 h after which the reaction mixture
  2. temperaturewas cooled to room temperature
  3. extractionextracted with CH2Cl2 (3×30 ml)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography over silica gel with 1:1 hexane/CH2Cl2

Sources & evidence

ORD record
ord-c1adbde60c044099ae80192304f452c2
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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