Methylhydrazine → HCID 14128011, compound

HRID 2351244Notes

Reaction equation

HRID 2351244 reaction equation
[C:1]([C:4](=[C:10](SC)[S:11][CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].[CH3:15][NH:16][NH2:17]>C(#N)C>[CH3:15][N:16]1[C:10]([S:11][CH3:12])=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:1]([CH3:2])=[N:17]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 4997384Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl ester

Product 1

HCID 14128011HCID 14128011, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 50 ml of acetonitrile is dissolved 7.5 g of ethyl 2-acetyl-3,3-bis(methylthio)acrylate. To the solution is added dropwise, while stirring at room temperature (15° C.), 1.8 g of methyl hydrazine over a period of 10 minutes, followed by heating for 7 hours under reflux. After completion of the reaction, the solvent is distilled off under reduced pressure. The residue is purified by means of silica gel column chromatography (eluent, n-hexane:ethyl acetate =4/1 to 2/1) to give 4.1 g of the title compound as an oil.

Workup

  1. additionTo the solution is added dropwise
  2. temperatureby heating for 7 hours
  3. temperatureunder reflux
  4. customAfter completion of the reaction
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by means of silica gel column chromatography (eluent, n-hexane:ethyl acetate =4/1 to 2/1)

Sources & evidence

ORD record
ord-923bf36ff2c049babf8fe1f369ed2e2a
Source dataset
uspto-grants-1989_10
Patent number
US04872901

Reaction notes

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