Semicarbazide hydrochloride → HCID 354307, compound

HRID 1736566Notes

Reaction equation

HRID 1736566 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-1carboxamide 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-72e55f74950f417cbd44712763e5e8bd
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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