2-BENZO[1,3]DIOXOL-5-YL-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER synthesis

4synthesis methods

Product Name:2-BENZO[1,3]DIOXOL-5-YL-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
CAS Number:248249-53-8
Molecular formula:C13H11NO4S
Molecular Weight:277.3

4-Thiazolecarboxylic acid, 2-(1,3-benzodioxol-5-yl)-4,5-dihydro-, ethyl ester, (4R)-

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2-BENZO[1,3]DIOXOL-5-YL-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER

248249-53-8
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$87.50/250mg

Yield:248249-53-8 81%

Reaction Conditions:

with manganese(IV) oxide in dichloromethane at 0; for 6 h;

Steps:

17 Example 17, Synthesis of ethyl 4-(benzo[3,4-d]1,3-dioxolan-5-yl)-3,5-thiazole carboxylate(Compound 22)

Ethyl (1R)-4-(benzo[3,4-d]1,3-dioxolan-5-yl)-3,5-thiazoline carboxylate prepared in Example 13(1.25g, 4.47mmol) was dissolved in methylene chloride(60mlitre), and the reaction solution was cooled down to 0°C. To this solution was added manganese oxide(3.89g, 44.76mmol), and the resulting mixture was stirred for 6 hours and filtered through cellite. The filtrate was concentrated, and to the residue was added n-hexane. The resulting mixture was stirred and filtered to give the title compound(1.0g, Yield 81%) as a white solid. 1H NMR (300MHz, CDCl3) : δ 1.45(t, 3H, J = 7.1 Hz), 4.46(q, 2H, J = 7.1 Hz), 6.06(s, 2H), 6.89(d, 1H, J = 7.9 Hz), 7.53(dd, 1H, J = 1.7, 8.0 Hz), 7.56(d, 1H, J = 1.7 Hz), 8.11(s, 1H)

References:

EP1073428,2004,B1 Location in patent:Page 27