Formaldehyde → 5-(Hydroxymethyl)uracil

HRID 342528

Reaktionsgleichung

Reaktionsgleichung von HRID 342528
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH2:9]=[O:10].[OH-].[K+]>O>[OH:10][CH2:9][C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 1174UracilHCID 14797Potassium Hydroxide

Produkt 1

HCID 781685-(Hydroxymethyl)uracilAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of uracil (9 g, 80.3 mmol), paraformaldehyde (3 g) and 0.42N potassium hydroxide (125 mL) was heated 90 hours at 50° C. The reaction mixture was diluted with water (350 mL), stirred with Dowex® 50 ion-exchange resin (30 g, H form, 100-200 mesh), filtered, concentrated in vacuo to a volume of 20 mL and refrigerated. The solids were collected and recrystallized from water (50 mL) to give 5-hydroxymethyl-2,4(1H,3H)-pyrimidinedione (9.5 g, 65.04 mmol), m.p. 260°-300° C. (dec).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo to a volume of 20 mL
  3. customThe solids were collected
  4. customrecrystallized from water (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-e1856cadb56d4369839b50b4722dc1d2
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859014

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