Pyrazole-1-carboxamidine monohydrochloride → 1-(2-(5,5-Dimethyl-2,4-dioxoimidazolidin-1-yl)ethyl)guanidine hydrochloride

HRID 2267289Notes

Reaction equation

HRID 2267289 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]([CH3:10])([CH3:9])[C:7](=[O:11])[NH:6][C:5]1=[O:12].[ClH:13].[N:14]1([C:19](N)=[NH:20])C=CC=N1>CC#N>[ClH:13].[CH3:10][C:8]1([CH3:9])[N:4]([CH2:3][CH2:2][NH:1][C:19]([NH2:20])=[NH:14])[C:5](=[O:12])[NH:6][C:7]1=[O:11]

Participants

4

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 1784294231-(2-(5,5-Dimethyl-2,4-dioxoimidazolidin-1-yl)ethyl)guanidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Amino-ethyl)-5,5-dimethyl-imidazolidine-2,4-dione (5.00 g., 29 mmol) and pyrazole-1-carboxamidine hydrochloride (4.28 g., 29 mmol) were added to MeCN (100 mL) and heated at reflux for 16 h. The mixture was cooled, the supernatent MeCN layer was decanted off, and the residual gum was washed with MeCN twice. The gum was dissolved in MeOH (100 mL) and concentrated to give the product as a foam. Yield=7.29 g., 100%.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. temperatureThe mixture was cooled
  4. customthe supernatent MeCN layer was decanted off
  5. washthe residual gum was washed with MeCN twice
  6. dissolutionThe gum was dissolved in MeOH (100 mL)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-54001ef4027140edabb213ee13f1308f
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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