Methylhydrazine → HCID 14128012, compound

HRID 2351245Notes

Reaction equation

HRID 2351245 reaction equation
[C:1]([C:4](=[C:10](SCC1C=CC=CC=1)[S:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].[CH3:27][NH:28][NH2:29]>C(#N)C>[CH3:27][N:28]1[C:10]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:1]([CH3:2])=[N:29]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 3791082HCID 3791082, compound

Product 1

HCID 14128012HCID 14128012, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 60 ml of acetonitrile is dissolved 10.0 g of ethyl 2-acetyl-3,3-bis(benzylthio)acrylate. To the solution is added dropwise, while stirring at room temperature (15° C.), 1.2 g of methyl hydrazine over a period of 10 minutes, followed by heating for 3 hours under reflux. Then, the solvent is distilled off under reduced pressure. The residue is purified by means of silica gel column chromatography (eluent, n-hexane:ethyl acetate=8/1) to give 5.8 g of the title compound as white crystals, m.p. 55° to 56° C.

Workup

  1. additionTo the solution is added dropwise
  2. temperatureby heating for 3 hours
  3. temperatureunder reflux
  4. distillationThen, the solvent is distilled off under reduced pressure
  5. customThe residue is purified by means of silica gel column chromatography (eluent, n-hexane:ethyl acetate=8/1)

Sources & evidence

ORD record
ord-1299fee31ef14aaf987631f51b56b77a
Source dataset
uspto-grants-1989_10
Patent number
US04872901

Reaction notes

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