ChemicalBook CAS DataBase List RARECHEM AL BI 1318

RARECHEM AL BI 1318 synthesis

14synthesis methods

Product Name:RARECHEM AL BI 1318
CAS Number:59937-01-8
Molecular formula:C12H11NO2S
Molecular Weight:233.29

ethyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate

70454-09-0

59937-01-8

GENERAL METHOD: 4-carboxythiazoline or 4-carboxyoxazoline (0.5 mmol) was dissolved in anhydrous DMF (1 mL), molecular sieves (4 ? , 100% wt) and copper(II) acetate (9.1 mg, 0.05 mmol). The reaction mixture was stirred at 120 °C for 10 to 24 h under an oxygen atmosphere (using an O2 balloon). After completion of the reaction, the reaction mixture was diluted with ethyl acetate, the organic layer was washed sequentially with water and brine, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel fast column chromatography to obtain the target product 4-carboxythiazole or 4-carboxyoxazole.

70-23-5
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$6.00/5g

2227-79-4 Synthesis

2227-79-4
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59937-01-8
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$43.00/250mg

Yield:59937-01-8 94%

Reaction Conditions:

in ethanol at 20; for 2 h;Reflux;

Steps:

85A Ethyl 2-phenylthiazole-4-carboxylate

A solution of benzothioamide (3.00 g, 21.87 mmol) in EtOH (70 mL) was treated dropwise with ethyl bromopyruvate (5.10 g, 26.2 mmol) and stirred at room temperature for 30 min before being heated at reflux for 1.5 h. The cooled mixture was diluted with ethyl acetate (200 mL), washed (aqueous NaHC0₃, brine), dried over anhydrous MgSO₄ and evaporated. The residue was purified on the ISCO using a REDISEP 80 g column (10 to 20% EtOAc-hexane) to give the title compound (4.82 g, 94%) as a yellow oil. LCMS (APCI): calcd for C₁₂H₁₂NO₂S [M+H]⁺ m/z 234.05, found 234.1. ¹H NMR (CDCl₃, 400 MHz) δ ppm: 8.14 - 8.19 (m, 1H), 7.98 - 8.07 (m, 2H), 7.41 - 7.51 (m, 3H), 4.46 (q, J= 7.2 Hz, 2H), 1.44 (t, J= 7.2 Hz, 3H)

References:

WO2013/163279,2013,A1 Location in patent:Paragraph 00226