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HomeProduct name listEthyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

  • CAS NO.:161797-99-5
  • Empirical Formula: C13H13NO3S
  • Molecular Weight: 263.31
  • MDL number: MFCD03700424
  • EINECS: 605-268-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate Structural

What is Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate?

The Uses of Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Ethyl 2-(4-Hydroxyphenyl)-4-methylthiazole-5-carboxylate is used in the synthesis of the major metabolites of Febuxostat (F229000), a xanthine oxidase/xanthine dehydrogenase inhibitor. Used for treatment of hyperuricemia and chronic gout. 40-120 mg/day febuxostat was proven effective in lowering serum urate levels when administered to manage hyperuricemia in patients with gout.

Synthesis

A mixture of 4-cyanophenol, NaOH, and ethanol was mixed in a pressure bottle while heated to 80° C. Hydrogen sulfide gas was then introduced, and the pressure increased to 30-60 psi until the thioamidation was determined to be complete by HPLC. Without isolating the thioamide product, HCl was added to the bottle until the pH was below 3.5, the H2S gas was removed, and the bottle was placed under a vacuum for 20 minutes at 30-40° C. The reaction was then heated to 70° C, and ethyl 2-chloroacetoacetate(1.1 eq.) was added to the reaction solution. The reaction was mixed under reflux for 2-3 hours, treated with enough H2O to dissolve the NaCl salt in the reaction mixture, cooled to room temperature, treated with enough water to precipitate the product, and the solid was collected by filtration. The precipitate was washed with water and dried at 80° C. with nitrogen bleeding to provide Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate. ethyl 2-(4-hydroxyphenyl)-4-methyl thiazole-5-carboxylate

Properties of Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Melting point: 180 ºC
Boiling point: 426.8±55.0 °C(Predicted)
Density  1.274
storage temp.  Sealed in dry,Room Temperature
solubility  DMSO (Slightly), Methanol (Very Slightly)
form  Solid
pka 8.56±0.15(Predicted)
color  Off-White
InChI InChI=1S/C13H13NO3S/c1-3-17-13(16)11-8(2)14-12(18-11)9-4-6-10(15)7-5-9/h4-7,15H,3H2,1-2H3
CAS DataBase Reference 161797-99-5(CAS DataBase Reference)

Safety information for Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate

InChIKey LOCYSKNNFCGDTR-UHFFFAOYSA-N
SMILES S1C(C(OCC)=O)=C(C)N=C1C1=CC=C(O)C=C1

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