ChemicalBook CAS DataBase List ETHYL 4-THIOMETHYLBENZOYLFORMATE

ETHYL 4-THIOMETHYLBENZOYLFORMATE synthesis

5synthesis methods

Product Name:ETHYL 4-THIOMETHYLBENZOYLFORMATE
CAS Number:62936-31-6
Molecular formula:C11H12O3S
Molecular Weight:224.28

100-68-5 Synthesis

100-68-5
338 suppliers
$9.00/1g

4755-77-5 Synthesis

4755-77-5
331 suppliers
$9.00/25g

62936-31-6
39 suppliers
$345.00/1g

Yield:62936-31-6 84%

Reaction Conditions:

Stage #1: Ethyl oxalyl chloride;aluminum (III) chloride in dichloromethane;
Stage #2: methyl-phenyl-thioether in dichloromethane at 10 - 25; for 2 h;

Steps:

3 Example 3

Example 3 (E)-3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)-N-thiazol-2-yl-acrylamide A mixture of aluminum chloride (412.65 g, 3.09 mol) in methylene chloride (1.11 L) was cooled to 0° C. and stirred until the solid material dissolved.. The reaction mixture was then slowly treated with ethyl oxalyl chloride (300 ML, 2.69 mol), and the resulting reaction mixture changed from yellow to orange in color.. The reaction mixture was then slowly treated with a solution of thioanisole (300 ML, 2.56 mol) in methylene chloride (244 ML) in small portions over 1 h.. During the addition of thioanisole, the reaction temperature was kept below 10° C. The resulting reaction mixture was allowed to warm to 25° C. where it was stirred for 1 h.. The reaction mixture was then cooled back to 0° C. and then slowly treated with ice/water (800 ML) over 1 h.. The reaction mixture was then transferred to a separatory funnel in one-liter portions.. The one-liter portions were continuously extracted with methylene chloride until the aqueous layer showed absence of product by thin layer cliromatography.. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford (4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (481.67 g, 84%) as a yellow liquid which was used without further purification: EI-HRMS m/e calcd for C11H12O3S (M+) 224.0507, found 224.0500.

References:

US6353111,2002,B1 Location in patent:Page column 21-22