Methylhydrazine → N,1-Dimethyl-N-phenylhydrazinethiocarboxamide

HRID 893872Notes

Reaction equation

HRID 893872 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>[CH3:12][N:13]([C:3]([N:2]([CH3:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:4])[NH2:14]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 2760019Methyl(phenyl)carbamothioyl chloride

Product 1

HCID 12881174N,1-Dimethyl-N-phenylhydrazinethiocarboxamideYield 83.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of N-methyl-N-phenylthiocarbamyl chloride (79.6 g, 0.43 mole) in 250 ml dry ether, a solution of 39.5 g (0.86 mole) 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 the mixture was filtered. The filtrate was evaporated to low volume and diluted with about 300 ml hexane. After stirring for a few hours the hexane layer was decanted. The hexane immiscible layer was reevaporated to remove organic solvents, giving the desired product, (70.0 g) as a thick orange liquid.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated to low volume
  3. additiondiluted with about 300 ml hexane
  4. stirringAfter stirring for a few hours the hexane layer
  5. customwas decanted
  6. customThe hexane immiscible layer was reevaporated
  7. customto remove organic solvents

Sources & evidence

ORD record
ord-f194c1d7cf394b3da3692c083f32c8af
Source dataset
uspto-grants-1981_08
Patent number
US04282031

Reaction notes

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