Hydrazine → HCID 849740, compound

HRID 1943901Notes

Reaction equation

HRID 1943901 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].[NH2:14][NH2:15]>CC(O)C>[NH2:2][C:1]1[NH:15][N:14]=[C:9]([S:10][CH3:11])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 2747745Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate

Product 1

HCID 849740HCID 849740, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of ethyl 2-cyano-3,3-bis(methylthio)acrylate (2.2 g, 10.1 mmol) and hydrazine (0.325 mL, 10.1 mmol) in 2-propanol (20 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (1:1) to give ethyl 5-amino-3-(methylthio)-1H-pyrazole-4-carboxylate (1.2 g, 59%) as a solid. m/z (APCI-pos) M+1=202.0.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated
  3. customThe crude product was purified by column chromatography
  4. washeluting with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-352e1399bcf04837a414212138d19090
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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