Hydrazine hydrate (1:1) → HCID 178509165, compound

HRID 1380514Notes

Reaction equation

HRID 1380514 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CS[C:19](SC)=[N:20][C:21]#[N:22].[OH2:25].[NH2:26][NH2:27]>C(#N)C>[NH2:22][C:21]1[NH:20][C:19]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:25])[CH2:2][CH2:3]2)=[N:26][N:27]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 178509165HCID 178509165, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As for Example 3, a mixture of 66.0 g (0.3 moles) of benzyl N-piperazinecarboxylate and 43.8 g (0.3 moles) of dimethyl cyanodithioiminocarbonate in 300 ml of acetonitrile was refluxed for 16 hours. After cooling, filtration and washing, 16.0 ml (0.32 moles) of hydrazine hydrate was added to the filtrate and the mixture was refluxed for 4 hours. Cooling, filtration, and washing with cold acetonitrile, then hexane gave 74.7 g of the desired product as colorless crystals, mp 157°-159° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperatureAfter cooling
  3. filtrationfiltration
  4. washwashing
  5. temperaturethe mixture was refluxed for 4 hours
  6. temperatureCooling
  7. filtrationfiltration
  8. washwashing with cold acetonitrile

Sources & evidence

ORD record
ord-7cad9bec42854b41aef28d605d4168ba
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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