Semicarbazide hydrochloride → HCID 354307, compound

HRID 487276Notes

Reaction equation

HRID 487276 reaction equation
Cl.[NH2:2][NH:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].[C:9]([C:11](C#N)=[C:12]([C:15]#[N:16])[C:13]#[N:14])#[N:10]>O>[C:9]([C:11]1[C:12]([C:13]#[N:14])=[C:15]([NH2:16])[N:3]([C:4]([NH2:6])=[O:5])[N:2]=1)#[N:10]

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 12635TetracyanoethyleneHCID 14798Sodium Hydroxide

Product 1

HCID 354307HCID 354307, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of semicarbazide hydrochloride (11.2 g, 0.1 mol), water (200 ml) and sodium hydroxide (4.0 g, 0.1 mol) cooled in an ice-bath was added dropwise tetracyanoethylene (12.8 g, 0.1 mol). The reaction mixture was warmed to room temperature, stirred for 1.5 hours and then allowed to stand for 24 hours. The white precipitate which formed during the course of the reaction was collected by filtration and washed with water to afford 15.6 g (89%) of 3-cyano-4-cyano-5-amino-1H-pyrazole-1-carboxamide as a white solid, m.p. 225° C. (dec.) when dried at 85° C. in high vacuum.

Workup

  1. temperaturecooled in an ice-bath
  2. waitto stand for 24 hours
  3. customThe white precipitate which formed during the course of the reaction
  4. filtrationwas collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-0cae6a20e988468495028c0f9c561ea1
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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