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

HRID 1923582Notes

Reaction equation

HRID 1923582 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:25]([OH:27])=[O:26])=[CH:23][N:24]=3)=[C:16]([CH3:29])[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:25]([OH:27])=[O:26])=[CH:23][N:24]=3)=[C:16]([CH3:29])[O:15][N:14]=2)=[N:11][CH:12]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 666436562-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acid

Product 1

HCID 666436102-{(E)-2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-vinyl}-thiazole-5-carboxylic acidYield 89%

Conditions

Temperature
90 °C

Procedure

Concentrated sulfuric acid (29 mL) was added to 2-{2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-thiazole-5-carboxylic acid (1.71 g, 4.9 mmol) then the mixture was heated at 90° C. for 10 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 (1.44 g, 89%) as a yellow solid. MS: m/e=330.0 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-16362e80c4bc43d688ce1ff74c475ef9
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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