Methylhydrazine → HCID 18690738, compound

HRID 1871204Notes

Reaction equation

HRID 1871204 reaction equation
[CH3:1][NH:2][NH2:3].[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12](=O)[C:13]([CH3:19])=[C:14](SC)[S:15][CH3:16]>C(#N)C>[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[C:12]1[C:13]([CH3:19])=[C:14]([S:15][CH3:16])[N:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 18690739HCID 18690739, compound

Product 1

HCID 18690738HCID 18690738, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

0.138 g (0.003 mol) of methyl hydrazine is added to a solution of 0.614 g (0.002 mol) of 1-(2,4-dichlorophenyl)-3,3-bis(methylthio)-2-methyl-2-propen-1-one in 10 ml of acetonitrile and the reaction mixture is heated at 80° C. for 8 hours. The mixture is then concentrated in vacuo and the residue is taken up in ether, washed with water and dried over sodium sulfate. After the ether phase has been concentrated by evaporation, the residue is purified by column chromatography over silica gel with hexane/ethyl acetate 2/1 as eluant. The desired product is obtained in a yield of 0.425 g (74.0%) in the form of a white solid having a melting point of 65-66° C. (recrystallised from hexane).

Workup

  1. concentrationThe mixture is then concentrated in vacuo
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter the ether phase has been concentrated by evaporation
  5. customthe residue is purified by column chromatography over silica gel with hexane/ethyl acetate 2/1 as eluant

Sources & evidence

ORD record
ord-a2672459cfd641f3942d1689c239e4c1
Source dataset
uspto-grants-2000_08
Patent number
US06103667

Reaction notes

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