Methylhydrazine → HCID 19025427, compound

HRID 1033172Notes

Reaction equation

HRID 1033172 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-8e47d64290f84438861828f755029b56
Source dataset
uspto-grants-1994_05
Patent number
US05310724

Reaction notes

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