2-Hydrazinylthiazole → HCID 68497561, compound

HRID 895575Notes

Reaction equation

HRID 895575 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][NH2:7].[CH2:8]([O:10][C:11](=[O:25])[CH:12]=[C:13](OCC)[CH2:14][CH:15](OCC)OCC)[CH3:9]>C(O)(=O)C>[CH2:8]([O:10][C:11](=[O:25])[CH2:12][C:13]1[N:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[N:7]=[CH:15][CH:14]=1)[CH3:9]

Participants

4

Reactant 2

HCID 119590662-HydrazinylthiazoleHCID 73164876HCID 73164876, compound

Product 1

HCID 68497561HCID 68497561, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of thiazol-2-ylhydrazine (2.2 g, 19.1 mmol) and 3,5,5-triethoxy-pent-2-enoic acid ethyl ester (70% purity, 7.1 g, 19.1 mmol) is refluxed in acetic acid overnight. Acetic acid is removed. To the residue is added NaHCO3 (aq.) (40 mL) and ethyl acetate (100 mL). The insoluble material is filtered. The organic layer is dried and solvent removed. The crude is subjected to column separation (hexane/ethyl acetate 3:1) to give (2-thiazol-2-yl-2H-pyrazol-3-yl)-acetic acid ethyl ester as an oil.

Workup

  1. customAcetic acid is removed
  2. additionTo the residue is added NaHCO3 (aq.) (40 mL) and ethyl acetate (100 mL)
  3. filtrationThe insoluble material is filtered
  4. customThe organic layer is dried
  5. customsolvent removed
  6. customThe crude is subjected to column separation (hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-55dd300b8682407d8fb2b632463192a9
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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