Sulfuric Acid → 2-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid

HRID 1923601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923601
S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:17]([CH:18](O)[CH2:19][C:20]3[S:21][C:22]([C:26]([OH:28])=[O:27])=[C:23]([CH3:25])[N:24]=3)=[CH:16][O:15][N:14]=2)=[N:11][CH:12]=1>>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:17](/[CH:18]=[CH:19]/[C:20]3[S:21][C:22]([C:26]([OH:28])=[O:27])=[C:23]([CH3:25])[N:24]=3)=[CH:16][O:15][N:14]=2)=[N:11][CH:12]=1

Komponenten

3

Edukt 2

HCID 1118Sulfuric AcidHCID 66643633HCID 66643633, Verbindung

Produkt 1

HCID 666437722-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acidAusbeute 61 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Concentrated sulfuric acid (27 mL) was added to 2-{2-[3-(5-fluoro-pyridin-2-yl)-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid (1.6 g, 4.6 mmol) then the mixture was heated at 90° C. for 20 min. After cooling to room temperature the mixture was poured into ice (200 g) and the precipitate was filtered off and dried to give the title product (930 mg, 61%) as a light yellow solid after trituration from ethyl acetate. MS: m/e=330.3 [M−H]−.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationthe precipitate was filtered off
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f0ffb4dac8a04610ad499dc7dfe07eb6
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178522B2

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