Hydrochloric Acid → 5-Hydroxy-5-[1-(1-butyl)-2-pyrrolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

HRID 66591

Reaktionsgleichung

Reaktionsgleichung von HRID 66591
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[K].I[CH2:8][CH2:9][CH2:10][CH3:11].[NH:12]1[C:20](=[O:21])[C:18](=[O:19])[C:16](=[O:17])[NH:15][C:13]1=[O:14].Cl>C(O)C.O1CCCC1>[OH:19][C:18]1([C:2]2[N:1]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][CH:3]=2)[C:16](=[O:17])[NH:15][C:13](=[O:14])[NH:12][C:20]1=[O:21]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5781AlloxanHCID 10962Butyl iodideHCID 241923201H-Pyrrole, potassium salt (1:1)

Produkt 1

HCID 132828935-Hydroxy-5-[1-(1-butyl)-2-pyrrolyl)-2,4,6-(1H,3H,5H)pyrimidinetrioneAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Potassium pyrrole (3.0 g., 0.03 mole), 1-iodobutane (9.2 g., 0.05 moles) and 10 ml. of tetrahydrofuran were combined and refluxed for 1.5 hours by which time the reaction mixture had become a thick mass. The reaction mixture was diluted with 30 ml. of water and extracted with 35 ml. of ether. The ether was back-washed with water, then added to a solution of anhydrous alloxan (4.8 g., 0.03 mole) obtained by heating in 50 ml. of ethanol. The ether was distilled away, 6 N hydrochloric acid (5 ml., 0.03 mole) was added, and the mixture refluxed for 3 minutes, cooled, evaporated to a gum, and triturated with water to afford title product [5.1 g.; m.p. 135 (dec); m/e 265].

Aufarbeitung

  1. temperaturerefluxed for 1.5 hours by which time the reaction mixture
  2. additionThe reaction mixture was diluted with 30 ml
  3. extractionof water and extracted with 35 ml
  4. washThe ether was back-washed with water
  5. customobtained
  6. temperatureby heating in 50 ml
  7. distillationThe ether was distilled away
  8. temperaturethe mixture refluxed for 3 minutes
  9. temperaturecooled
  10. customevaporated to a gum
  11. customtriturated with water

Quellen und Nachweise

ORD-Eintrag
ord-9d9bd77c87eb40fe84919dff7e53f81f
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04342771

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