Ethyl bromopyruvate → Ethyl 2-hydrazinyl-1,3-thiazole-4-carboxylate

HRID 2196517Notes

Reaction equation

HRID 2196517 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].Br[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>O1CCOCC1>[NH:2]([C:3]1[S:4][CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]=1)[NH2:1]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2723789Thiosemicarbazide

Product 1

HCID 14181283Ethyl 2-hydrazinyl-1,3-thiazole-4-carboxylateYield 27%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of thiosemicarbazide (911 mg, 10 mmol) in dioxane (10 mL) was added ethyl bromopyruvate (1258 μl, 10.00 mmol). The resulting solution was allowed to stir for 16 h at room temperature, then for 2 h at 60° C. Solvent was evaporated and the residue was purified by silica gel column chromatography with gradient of methanol (0-10%) in CH2Cl2 to afford 28 (500 mg, 27%) as an orange solid. LRMS (ESI): calc. 187.1; found 188.1 (MH)+.

Workup

  1. waitfor 2 h at 60° C
  2. customSolvent was evaporated
  3. customthe residue was purified by silica gel column chromatography with gradient of methanol (0-10%) in CH2Cl2

Sources & evidence

ORD record
ord-d224432e6f87471a9c24d7b59260bd69
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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