Acetone → Febuxostat

HRID 870885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870885
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[S:15][C:16]([C:20]([O:22]CC)=[O:21])=[C:17]([CH3:19])[N:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([CH3:13])[CH3:12])#[N:2].CC(C)=O.[OH-].[Na+].Cl>C(OCC)(=O)C.O>[CH3:19][C:17]1[N:18]=[C:14]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[C:3]([C:1]#[N:2])[CH:4]=2)[S:15][C:16]=1[C:20]([OH:22])=[O:21]

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 98845495-Thiazolecarboxylic acid, 2-(3-cyano-4-(2-methylpropoxy)phenyl)-4-methyl-, ethyl ester

Produkt 1

HCID 134018FebuxostatAusbeute 2,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate (50.0 g), acetone (500 mL), water (200 mL), and sodium hydroxide (6.96 g) were placed into a round bottom flask and heated to reflux. The mixture was maintained under reflux until reaction completion. After the reaction was completed, the mass was cooled to about 25° C., water (500 mL) and ethyl acetate (500 mL) were added, and the pH was adjusted to about 1 to 2 with hydrochloric acid (10.3 mL). The organic layer was separated and the aqueous layer was extracted into ethyl acetate (250 mL). The ethyl acetate layer was washed with water (300 mL). The ethyl acetate layer was distilled completely under vacuum below 60° C. The residue was dried at about 60° C. under vacuum to a constant weight to yield 1.0 g of the title compound. Purity by HPLC: 98.9%.

Aufarbeitung

  1. temperatureheated to reflux
  2. temperatureThe mixture was maintained
  3. temperatureunder reflux until reaction completion
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted into ethyl acetate (250 mL)
  6. washThe ethyl acetate layer was washed with water (300 mL)
  7. distillationThe ethyl acetate layer was distilled completely under vacuum below 60° C
  8. customThe residue was dried at about 60° C. under vacuum to a constant weight

Quellen und Nachweise

ORD-Eintrag
ord-09a7848db7794e04a352488bcf3ae445
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969582B2

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