Methylhydrazine → N,1-Dimethyl-N-phenylhydrazinethiocarboxamide

HRID 444387Notes

Reaction equation

HRID 444387 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[S:4].[CH3:12][NH:13][NH2:14]>CCOCC>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([N:13]([CH3:12])[NH2:14])=[S:4]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 2760019Methyl(phenyl)carbamothioyl chloride

Product 1

HCID 12881174N,1-Dimethyl-N-phenylhydrazinethiocarboxamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of N-methyl-N-phenylthiocarbamyl chloride 79.6 g (0.43 m) in 250 ml dry ether, a solution of 39.5 g (0.86 m) methylhydrazine in 100 ml of dry ether was added dropwise with stirring below 10° C. The reaction temperature was allowed to increase to room temperature and filtered. The filtrate was evaporated to low volume and diluted with ~300 ml hexane. After stirring for a few hours the hexane layer was decanted. The hexane immiscible layer was reevacuated to remove organic solvents, giving the desired product, 70.0 g as a thick orange liquid.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to low volume
  3. additiondiluted with ~300 ml hexane
  4. stirringAfter stirring for a few hours the hexane layer
  5. customwas decanted
  6. customto remove organic solvents

Sources & evidence

ORD record
ord-715f2e5bab204598ae2eeb113c0c7965
Source dataset
uspto-grants-1981_04
Patent number
US04264502

Reaction notes

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