Guanidine Hydrochloride → HCID 178440788, compound

HRID 486109Notes

Reaction equation

HRID 486109 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC(C)([O-])C.[K+].[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([CH:27]=[C:28]2[O:32][C:31](SC)=[N:30][C:29]2=[O:35])[CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])([CH3:15])[CH3:14]>C(O)C>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([CH:27]=[C:28]2[O:32][C:31]([NH:4][C:3]([NH2:5])=[NH:2])=[N:30][C:29]2=[O:35])[CH:19]=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:21]=1[OH:22])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 54084465HCID 54084465, compound

Product 1

HCID 178440788HCID 178440788, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.0 g (0.021 mole) of guanidine hydrochloride in 75 mL of ethanol is cooled in ice and treated in portions with 2.2 g (0.020 mole) of potassium tert-butoxide. The mixture is stirred for 15 minutes, and then rapidly filtered into a suspension of 4.6 g (0.013 mole) of 5-[[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(methylthio)-4(5H)-oxazolone in 75 mL of ethanol. The new reaction mixture is stirred at reflex for 3 hours, then cooled and filtered. The filtrate is evaporated 50% and added to 500 g of ice and water. The precipitated solid is filtered, washed with water, and dissolved in 200 mL of ethyl acetate. The solution is washed with brine (3×200 mL), dried (anhydrous sodium sulfate), and evaporated. The residue is chromatographed over silica gel, using elution with 10% acetonitrile in ethyl acetate. The purified product, [5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro- 4-oxo-2-oxazolyl]guanidine, is 2.6 g (55% yield). A sample recrystallized from aqueous acetonitrile has mp 258°-dec.

Workup

  1. stirringThe new reaction mixture is stirred at reflex for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate is evaporated 50%
  5. additionadded to 500 g of ice and water
  6. filtrationThe precipitated solid is filtered
  7. washwashed with water
  8. dissolutiondissolved in 200 mL of ethyl acetate
  9. washThe solution is washed with brine (3×200 mL)
  10. dry with materialdried (anhydrous sodium sulfate)
  11. customevaporated
  12. customThe residue is chromatographed over silica gel
  13. washelution with 10% acetonitrile in ethyl acetate
  14. customA sample recrystallized from aqueous acetonitrile

Sources & evidence

ORD record
ord-8dab2cd680024bd5ad4a3be44b8ba1c1
Source dataset
uspto-grants-1994_03
Patent number
US05290800

Reaction notes

Loading…