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

HRID 1923601Notes

Reaction equation

HRID 1923601 reaction equation
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

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 66643633HCID 66643633, compound

Product 1

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

Conditions

Temperature
90 °C

Procedure

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]−.

Workup

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

Sources & evidence

ORD record
ord-f0ffb4dac8a04610ad499dc7dfe07eb6
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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