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ChemicalBook CAS DataBase List 2-PHENYLTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER
7113-02-2

2-PHENYLTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER synthesis

9synthesis methods
-

Yield:7113-02-2 77%

Reaction Conditions:

in tetrahydrofuran; for 18 h;Reflux;

Steps:

3A Methyl 2-phenylthiazole-4-carboxylate

A solution of benzothioamide (4.0g, 29.2 mmol) in THF (80 mL) was treated dropwise with methyl bromopyruvate (7.6g, 39 mmol) and heated at reflux for 18 hours. The reaction was then concentrated under vacuum, diluted with ethyl acetate, washed with water (lx), brine (lx) and dried over anhydrous magnesium sulfate. The residue obtained after concentration was purified by silica gel chromatography (4.5 x 1 1 cm, 20% AcOEt/ toluene), followed by a second purification with 20% AcOEt/hexane. The title material was obtained after concentration as a yellow oil (5.25, 77%). 1H NMR (CDCl3, 400 MHz): 8.14 (s, 1H) 8.00 (m, 2H) 7.46-7.42 (m, 3H) 4.43 (q, J=7.0 Hz, 2H) 1.42 (t, J=7.3 Hz, 3H).

References:

WO2013/163279,2013,A1 Location in patent:Paragraph 00144

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