Ethanol → HCID 178470113, compound

HRID 1858506Notes

Reaction equation

HRID 1858506 reaction equation
[C:1](=[S:4])([S-:3])[NH2:2].[NH4+].Br[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(O)C.C(OCC)(=O)C>O>[CH2:12]([O:11][C:9]([C:8]1[N:2]=[C:1]([SH:3])[S:4][CH:7]=1)=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 66144Ethyl bromopyruvateHCID 11083854Ammonium dithiocarbamate

Product 1

HCID 178470113HCID 178470113, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of ammonium dithiocarbamate ##STR5## (1.10 g) in water (10 ml) were added ethyl bromopyruvate (1.95 g) and ethanol (5 ml) at ice-cooling. After stirring at room temperature for 1 hour, the mixture was poured into a mixture of water and ethyl acetate. The separated organic layer was washed with saturated sodium chloride solution (×2), dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give 4-ethoxycarbonyl-2-mercaptothiazole (1.21 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with saturated sodium chloride solution (×2)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7e566ba8343c416aa2ee8a6f63a4abae
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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