Keto-pantoyllactone → 3,4-diamino-6-(1',1'-dimethyl-2'-hydroxyethyl)-1,2,4,-triazin-5(4H)-one hydrochloride

HRID 843608Notes

Reaction equation

HRID 843608 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:6][O:5][C:4](=[O:7])[C:3]1=O.[ClH:10].[NH2:11][NH:12][C:13]([NH:15][NH2:16])=[NH:14].O>C(O)C>[ClH:10].[NH2:14][C:13]1[N:15]([NH2:16])[C:4](=[O:7])[C:3]([C:2]([CH3:9])([CH3:1])[CH2:6][OH:5])=[N:11][N:12]=1

Participants

5

Reactant 3

HCID 39Keto-pantoyllactoneHCID 962WaterHCID 178479531HCID 178479531, compound

Product 1

HCID 226111153,4-diamino-6-(1',1'-dimethyl-2'-hydroxyethyl)-1,2,4,-triazin-5(4H)-one hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dihydro-4,4-dimethyl-2,3-furandione (2 g, 15.6 mmole) and 1,3-diaminoguanidine monohydrochloride (12.96 g, 15.61 mmole) were dissolved in ethanol and the resulting solution heated to reflux temperatures. To the refluxing reaction mixture, was added water until a clear solution was obtained. The mixture was then refluxed overnight, cooled to room temperature and stored at −20° C. overnight. The product which separated was filtered and dried. It was crystallized from a mixture of ethanol and water to give 3,4-diamino-6-(1′,1′-dimethyl-2′-hydroxyethyl)-1,2,4-triazin-5(4H)-one hydrochloride (2.24 g, 61%), m.p. 221-222° C. (dec).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureto reflux temperatures
  3. customTo the refluxing reaction mixture
  4. customwas obtained
  5. temperatureThe mixture was then refluxed overnight
  6. customThe product which separated
  7. filtrationwas filtered
  8. customdried
  9. customIt was crystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-862067304a844252aa24074a14206b26
Source dataset
uspto-grants-2002_04
Patent number
US06380192B1

Reaction notes

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