4-Sulfanylidene-1,3-thiazolidin-2-one → HCID 178518170, compound

HRID 1620669Notes

Reaction equation

HRID 1620669 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[OH:8].S=[C:10]1[CH2:14][S:13][C:12](=[O:15])[NH:11]1>C(O)C>[OH:8][C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]1[NH:1][C:10]1[CH2:14][S:13][C:12](=[O:15])[N:11]=1

Participants

4

Reactant 2

HCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 7057408(1S,2S)-2-aminocyclohexanol

Product 1

HCID 178518170HCID 178518170, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1S,2S)-2-aminocyclohexanol (1.00 g) in ethanol (30 mL) was added 4-thioxo-1,3-thiazolidin-2-one (1.17 g), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (786 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 (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6a624ce6b8474975b58510cb04dfc5d7
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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