Pentanenitrile, 4,4-dimethyl-3-oxo- → HCID 9794416, compound

HRID 2400155Notes

Reaction equation

HRID 2400155 reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[C:10]([NH:13][NH2:14])([NH2:12])=[NH:11].[ClH:15]>CO.C(O)(=O)C>[ClH:15].[NH2:9][C:8]1[N:13]([C:10]([NH2:12])=[NH:11])[N:14]=[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:7]=1

Participants

5

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 178418668HCID 178418668, compound

Product 1

HCID 9794416HCID 9794416, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1.26 g of pivaloylacetonitrile and 1.37 g of aminoguanidine hydrochloride in 15 ml of methanol and 15 ml of acetic acid was heated under reflux for 5 hours. The solvents were removed by distillation under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent: chloroform/methanol=5/1) and then recrystallized from ethanol-ether to obtain 0.74 g of 5-amino-3-(1,1-dimethylethyl)-1H-pyrazole-1-carboxamidine hydrochloride having the following physico-chemical properties:

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solvents were removed by distillation under reduced pressure
  3. customthe resulting residue was purified by silica gel chromatography (eluent: chloroform/methanol=5/1)
  4. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-f592540b52d54710847decb12ae8a072
Source dataset
uspto-grants-1995_09
Patent number
US05453514

Reaction notes

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