Dimethyl Sulfoxide → 2-Thiouracil-5-carboxylic acid

HRID 482180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482180
CC(C)([O-])C.[K+].CS(C)=O.CC[O:13][C:14]([C:16]1[C:22](=[O:23])[NH:21][C:19](=[S:20])[NH:18][CH:17]=1)=[O:15]>CO>[C:14]([C:16]1[C:22](=[O:23])[NH:21][C:19](=[S:20])[NH:18][CH:17]=1)([OH:15])=[O:13]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 735952Ethyl 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 30020412-Thiouracil-5-carboxylic acidAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Potassium tertiary butoxide (43.7 g, 389 mmol) and dimethyl sulfoxide (400 ml) were put in a 2-L egg-plant type flask to make a solution, ethyl 2-thiouracil-5-carboxylate (5.0 g, 25.0 mmol) was slowly added dropwise to the solution, and the mixture was subjected to reaction at room temperature for 1 hour. After the completion of the reaction, methanol (500 ml) was added to the reaction mixture, and the precipitate deposited was filtered. The resultant precipitate was dissolved in water, and hydrochloric acid was added to this solution to give 5-carboxy-2-thiouracil (2.54 g) as a light yellow solid.

Aufarbeitung

  1. additionwas slowly added dropwise to the solution
  2. customthe mixture was subjected to reaction at room temperature for 1 hour
  3. additionwas added to the reaction mixture
  4. filtrationthe precipitate deposited was filtered
  5. dissolutionThe resultant precipitate was dissolved in water
  6. additionhydrochloric acid was added to this solution

Quellen und Nachweise

ORD-Eintrag
ord-f896796e32f74b0fb3910bb72187f79d
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795497

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