Sodium Hydroxide → (5-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanone

HRID 2184795Notes

Reaction equation

HRID 2184795 reaction equation
[N+]([O-])(O)=O.[NH2:5][NH:6][C:7]([NH2:9])=N.CN([CH:13]=[C:14]([C:17](=[O:23])[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)C#N)C.[OH-].[Na+]>C(O)C>[NH2:9][C:7]1[C:14]([C:17]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[O:23])=[CH:13][NH:5][N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3743025α-[(Dimethylamino)methylene]-β-oxo-2-thiophenepropanenitrileHCID 178513186HCID 178513186, compound

Product 1

HCID 11550150(5-Amino-1H-pyrazol-4-yl)(thiophen-2-yl)methanoneYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of aminoguanidine nitrate (17.1, 125 mmol) and α-[(dimethylamino)methylene]-β-oxo-2-thiophenepropanenitrile (3) (20.6 g, 100 mmol) in commercial absolute ethanol (120 mL) is added 10N NaOH (5 g of solid NaOH in 12.5 mL of water). The reaction mixture is refluxed for 6 hrs and the solvents removed at reduced pressure on a rotary evaporator. Water (250 mL) is added and an initial precipitate forms and is filtered (13.3 g, 68.8 mmol, 69%). On further standing the aqueous layer deposits an additional quantity of the titled compound (3.42 g, 17.7 mmol, 18%), yielding product (4) as a tan solid (total 16.72 g, 86.5 mmol, 87%).

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hrs
  2. customthe solvents removed at reduced pressure on a rotary evaporator
  3. additionWater (250 mL) is added
  4. filtrationan initial precipitate forms and is filtered (13.3 g, 68.8 mmol, 69%)

Sources & evidence

ORD record
ord-02547df6c1a84bc5b44016f0fa6af5a8
Source dataset
uspto-grants-2002_06
Patent number
US06399621B1

Reaction notes

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