4-Sulfanylidene-1,3-thiazolidin-2-one → HCID 178484587, compound

HRID 1620651Notes

Reaction equation

HRID 1620651 reaction equation
[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[C@@H:4]([CH2:6][OH:7])[NH2:5].S=[C:11]1[CH2:15][S:14][C:13](=[O:16])[NH:12]1>C(O)C>[O:16]=[C:13]1[N:12]=[C:11]([NH:5][C@@H:4]([C:3]([N:2]([CH3:9])[CH3:1])=[O:8])[CH2:6][OH:7])[CH2:15][S:14]1

Participants

4

Reactant 2

HCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 86678816HCID 86678816, compound

Product 1

HCID 178484587HCID 178484587, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N,N-dimethyl-D-serinamide (645 mg) in ethanol (20 mL) was added 4-thioxo-1,3-thiazolidin-2-one (650 mg), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and the obtained powder was washed with ethyl acetate to give the title compound (799 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  5. washthe obtained powder was washed with ethyl acetate

Sources & evidence

ORD record
ord-f4dd2c4b83f1469284f7d2cac54a6354
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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