4-Sulfanylidene-1,3-thiazolidin-2-one → HCID 178518185, compound

HRID 1620724Notes

Reaction equation

HRID 1620724 reaction equation
[NH2:1][C@H:2]1[C@H:7]([OH:8])[CH2:6][O:5][CH2:4][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][O:5][CH2:4][CH2:3]2)[CH2:14][S:13]1

Participants

4

Reactant 2

HCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 54857363trans-4-Aminotetrahydropyran-3-ol

Product 1

HCID 178518185HCID 178518185, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-amino-1,5-anhydro-2,3-dideoxy-threo-pentitol (3.20 g) in ethanol (100 mL) was added 4-thioxo-1,3-thiazolidin-2-one (3.63 g), and the mixture was heated under reflux overnight. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.36 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-69d1c4dd78ae46ef89d5de3501e7aa93
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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