Methylhydrazine → HCID 19025427, compound

HRID 1030970Notes

Reaction equation

HRID 1030970 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]=[S:13].[CH3:14][NH:15][NH2:16]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[S:13])[N:15]([CH3:14])[NH2:16]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 27577362-chloro-1-isothiocyanato-4-nitrobenzene

Product 1

HCID 19025427HCID 19025427, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 60.0 g (0.280 mole) of 2-chloro-4-nitrophenyl isothiocyanate in 500 ml of ethanol was added 12.9 g (0.280 mole) of methylhydrazine. This mixture was heated and was stirred at 65° C. for approximately 18 hours. The mixture was then heated to reflux and was cooled. A solid had formed and was collected by filtration. The filter cake was rinsed with aqueous ethanol and was dried under reduced pressure to yield 59.0 g of 4-(2-chloro-4-nitrophenyl)-2-methyl-3-thiosemicarbazide, mp 164°-167° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureThis mixture was heated
  2. temperatureThe mixture was then heated
  3. temperatureto reflux
  4. temperaturewas cooled
  5. customA solid had formed
  6. filtrationwas collected by filtration
  7. washThe filter cake was rinsed with aqueous ethanol
  8. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-e0800a43804c4bc9a5f3dc7c01df1a49
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

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