4-Sulfanylidene-1,3-thiazolidin-2-one → HCID 178518187, compound

HRID 1620744Notes

Reaction equation

HRID 1620744 reaction equation
[NH2:1][C@H:2]1[C@H:7]([OH:8])[CH2:6][CH2:5][O:4][CH2:3]1.S=[C:10]1[CH2:14][S:13][C:12](=[O:15])[NH:11]1>C(O)C>[O:15]=[C:12]1[N:11]=[C:10]([NH:1][C@H:2]2[C@H:7]([OH:8])[CH2:6][CH2:5][O:4][CH2:3]2)[CH2:14][S:13]1

Participants

4

Reactant 2

HCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 72207589(3R,4R)-3-Aminotetrahydro-2H-pyran-4-ol

Product 1

HCID 178518187HCID 178518187, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-amino-1,5-anhydro-2,4-dideoxy-threo-pentitol (1.09 g) in ethanol (100 mL) was added 4-thioxo-1,3-thiazolidin-2-one (1.28 g), and the mixture was heated under reflux for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate) to give the title compound (1.00 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate)

Sources & evidence

ORD record
ord-29bec97a851947e88a08e087103a9c1b
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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