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

HRID 1923574Notes

Reaction equation

HRID 1923574 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)=[C:16]([CH3:30])[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)=[C:16]([CH3:30])[O:15][N:14]=2)=[N:11][CH:12]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 666437052-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 666436302-{(E)-2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid

Conditions

Temperature
90 °C

Procedure

Concentrated sulfuric acid (9.3 mL) was added to 2-{2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid (574 mg, 1.58 mmol) then the mixture was heated at 90° C. for 10 min. After cooling to room temperature the mixture was poured into ice (100 g) and the precipitate was filtered off and dried to give the title product. (471 mg, 86%) as a yellow solid. MS: m/e=344.1 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-bd332fe864274a1a989b2bb4a503e54b
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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