Methanol → 1,6-Dihydro-5(4H)-pyrimidinone O-(2-propenyl)oxime monohydrochloride

HRID 129819

Reaktionsgleichung

Reaktionsgleichung von HRID 129819
O.[ClH:2].Cl.[NH2:4][CH2:5][C:6]([CH2:8][NH2:9])=O.Cl.[CH2:11]([O:14][NH2:15])[CH:12]=[CH2:13].[CH3:16]O>>[ClH:2].[CH2:11]([O:14][N:15]=[C:6]1[CH2:8][NH:9][CH:16]=[N:4][CH2:5]1)[CH:12]=[CH2:13]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 190837391,3-Diaminopropan-2-one--hydrogen chloride--water (1/2/1)

Produkt 1

HCID 736056121,6-Dihydro-5(4H)-pyrimidinone O-(2-propenyl)oxime monohydrochlorideAusbeute 57 %

Versuchsvorschrift

1,3-Diaminoacetone dihydrochloride monohydrate (2.00 g, 11.2 mmol) was dissolved in refluxing methanol and O-2-propenylhydroxylamine hydrochloride (2.40 g, 21.9 mmol) was added. After refluxing for 96 hours the solvent was evaporated. The crude product was dissolved in methanol and an excess of trimethylorthoformate was added to the reaction mixture which was heated to reflux. After 48 hours the solvent was removed in vacuo. Crystallization from methanol/ethyl acetate afforded 1.20 g (57%) of white material. Mp. 164.5° C.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter refluxing for 96 hours the solvent
  3. customwas evaporated
  4. dissolutionThe crude product was dissolved in methanol
  5. additionan excess of trimethylorthoformate was added to the reaction mixture which
  6. temperaturewas heated to reflux
  7. customAfter 48 hours the solvent was removed in vacuo
  8. customCrystallization from methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-aca0a4fbaa8c4026b4de06b57a50d53a
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470856

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