Hydrazinium chloride → HCID 849740, compound

HRID 1696191Notes

Reaction equation

HRID 1696191 reaction equation
[C:1]([C:3](=[C:9](SC)[S:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].Cl.[NH2:15][NH2:16].C([O-])(=O)C.[Na+]>C(O)C>[NH2:2][C:1]1[NH:16][N:15]=[C:9]([S:10][CH3:11])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 115031Hydrazinium chlorideHCID 517045Sodium AcetateHCID 2747745Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate

Product 1

HCID 849740HCID 849740, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-cyano-3,3-bis(methylthio)-acrylate (40 g), hydrazine hydrochloride (12.6 g) and sodium acetate (22.6 g) in ethanol was stirred at 90° C. for 2 hour. After cooling to room temperature, the reaction mixture was concentrated in vacuo, and to the residue were added water and ethyl acetate. The organic layer was separated, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and to the residue was added ethyl acetate and hexane. The precipitates were collected by filtration and dried to give 5-amino-4-ethoxycarbonyl-3-methylthio-1H-pyrazole (17.4 g, yield: 47%) as a colorless solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionto the residue were added water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. additionto the residue was added ethyl acetate and hexane
  8. filtrationThe precipitates were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-1dda29ae6de64303a35e1d972ad4658d
Source dataset
uspto-grants-2012_04
Patent number
US08163759B2

Reaction notes

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