Hydroxyamine hydrochloride → 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone

HRID 1459

Reaktionsgleichung

Reaktionsgleichung von HRID 1459
[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20]#[CH:21])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](C=O)[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].Cl.[NH2:24][OH:25]>C(O)C>[CH2:1]([C:3]1[C:4](=[O:22])[N:5]([CH2:19][C:20]#[CH:21])[C:6]([C:11]2[CH2:12][C:13](=[N:24][OH:25])[CH:14]=[CH:15][CH:16]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 196906845,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone

Produkt 1

HCID 1363783855,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinoneAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 100 mL RBF were charged 1.1 g (3.7 mmol) of 5,6-diethyl-2-(3-formyl-phenyl)-3-propargyl-4(3H)-pyrimidinone, 0.52 g (7.5 mmol) of hydroxylamine hydrochloride and 50 mL of ethanol. The reaction mixture was refluxed for 17 hours. The ethanol was removed in vacuo and ether and ethyl acetate were added to the residue. The organics were washed 3 times with water. The organic layer was gravity filtered to remove 0.22 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139). The organic layer was dried over MgSO4 and concentrated to yield a further 0.67 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139) as a white solid. A combined yield of 77.6% was obtained. 1H-NMR (CDCl3) 1.25(6H,m); 2.35(1H,t); 2.65(4H,m); 4.6(2H,d); 7.49-8.15(4H,m); 8.7(1H,s)

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 17 hours
  2. customThe ethanol was removed in vacuo and ether and ethyl acetate
  3. additionwere added to the residue
  4. washThe organics were washed 3 times with water
  5. filtrationfiltered
  6. customto remove 0.22 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db525fc7ca504fc7b7efbfba048e0449
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726124

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