| Identification | More | [Name]
Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate | [CAS]
160844-75-7 | [Synonyms]
Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate | [EINECS(EC#)]
927-913-5 | [Molecular Formula]
C18H20N2O3S | [MDL Number]
MFCD09833701 | [Molecular Weight]
344.43 | [MOL File]
160844-75-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
176 °C | [Boiling point ]
497.1±55.0 °C(Predicted) | [density ]
1.22 | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly, Heated), Methanol (Very Slightly, Heated) | [form ]
Solid | [pka]
1.02±0.10(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C18H20N2O3S/c1-5-22-18(21)16-12(4)20-17(24-16)13-6-7-15(14(8-13)9-19)23-10-11(2)3/h6-8,11H,5,10H2,1-4H3 | [InChIKey]
OGAZOYHQFBSRMC-UHFFFAOYSA-N | [SMILES]
S1C(C(OCC)=O)=C(C)N=C1C1=CC=C(OCC(C)C)C(C#N)=C1 | [CAS DataBase Reference]
160844-75-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder | [Uses]
Ethyl 2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate is an impurity 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]
CarboxylatePotassium carbonate (300 g, 2.17 mol) and isobutyl bromide (142.7 g, 1.041 mol) were added to a solution of ethyl-2-(3-cyano-4-hydroxyphenyl)-4-methyl-5-thiazole carboxylate (100 g, 0.347 mol) in dimethylformamide (300 mL), and the reaction mixture was heated at a temperature of about 75°C for about 8 hours. After completion of the reaction, the reaction mixture was cooled to about 40°C, and water was added. The reaction mixture was further cooled to about 0°C and stirred for about 1 hour. The solid thus obtained was filtered, washed with water, and dried to give Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate. (Yield: 11 lg, 92.9%)
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