Hydrazine hydrate (1:1) → HCID 178509162, compound

HRID 1380512Notes

Reaction equation

HRID 1380512 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:3][CH:2]=1.CS[C:16](SC)=[N:17][C:18]#[N:19].O.[NH2:23][NH2:24]>C(O)C>[NH2:19][C:18]1[NH:17][C:16]([N:11]2[CH2:12][CH2:13][N:8]([CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:9][CH2:10]2)=[N:23][N:24]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 8087151-((Pyridin-4-yl)methyl)piperazine

Product 1

HCID 178509162HCID 178509162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 17.7 g (0.1 mole) amount of 1-(4-pyridylmethyl)piperazine (prepared as described above) was dissolved in 25 ml of ethanol and then added dropwise over 30 minutes to a stirred solution of 14.6 g (0.1 mole) of dimethyl cyanodithioiminocarbonate in 125 ml of ethanol. The mixture was refluxed for 20 hours, the evolved gas being led into a sodium hypochlorite trap, for the first 3 hours. Then 6.0 ml (0.12 mole) of hydrazine hydrate was added into the refluxing reaction mixture through the condenser and the mixture was refluxed for 6 hours longer. The mixture was evaporated to a solid residue which was recrystallized with ether and gave 25.8 g of the product of the Example as pale yellow crystals, mp 191°-193° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. customthe evolved gas being led into a sodium hypochlorite trap, for the first 3 hours
  3. temperaturethe mixture was refluxed for 6 hours longer
  4. customThe mixture was evaporated to a solid residue which
  5. customwas recrystallized with ether

Sources & evidence

ORD record
ord-f765145645ba4a8494019f878789afff
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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