Sulfuric Acid → HCID 66643663, compound

HRID 1923567Notes

Reaction equation

HRID 1923567 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]([C:10]1[S:14][C:13]([CH2:15][CH:16](O)[C:17]2[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][O:20][C:21]=2[CH3:22])=[N:12][C:11]=1[CH3:30])=[O:9]>C(=O)(O)[O-].[Na+]>[CH3:6][O:7][C:8]([C:10]1[S:14][C:13](/[CH:15]=[CH:16]/[C:17]2[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][O:20][C:21]=2[CH3:22])=[N:12][C:11]=1[CH3:30])=[O:9]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 66643863HCID 66643863, compound

Product 1

HCID 66643663HCID 66643663, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

Concentrated sulfuric acid (5 mL) was added to 2-[2-hydroxy-2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid methyl ester (200 mg, 0.56 mmol) then the mixture was heated at 90° C. for 10 min. The solution was carefully dropped into saturated sodium bicarbonate solution (100 mL) then extracted with ether. The combined organic extracts were dried, filtered and concentrated, to give the title compound (160 mg, 84%) as a yellow oil which solidified on standing to a yellow solid. This material was used directly without further purification. MS: m/e=341.1 [M+H]+.

Workup

  1. extractionthen extracted with ether
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7cbcbb545cd24bcb949ebb295c8fee24
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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