ChemicalBook CAS DataBase List Ethyl thiazole-2-carboxylate

Ethyl thiazole-2-carboxylate synthesis

3synthesis methods

Product Name:Ethyl thiazole-2-carboxylate
CAS Number:14527-42-5
Molecular formula:C6H7NO2S
Molecular Weight:157.19

79265-30-8

541-41-3

14527-42-5

General procedure for the preparation of ethyl 2-thiazolecarboxylate: a solution of 2-(trimethylsilyl)thiazole (135 g, 858.1 mmol) in toluene (1350 mL) was slowly added to a solution of ethyl chloroformate (98.4 mL, 1.03 mol) in toluene (1350 mL) over a period of 15 minutes. The reaction mixture was stirred continuously at 22°C for 2 hours. Subsequently, the reaction solution was poured into 25% (wt/wt) aqueous sodium carbonate solution (5 L) and stirring was continued for 30 min. The organic layer was separated and the aqueous layer was subjected to secondary extraction with dichloromethane (2 x 1 L). All organic layers were combined and the solvents were evaporated under reduced pressure to give ethyl 2-thiazolecarboxylate (134 g, 99% yield).ES/MS m/z 158 (M + 1)+.

79265-30-8 Synthesis

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541-41-3
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14527-42-5
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$9.00/100mg

Yield: 99%

Reaction Conditions:

Stage #1:2-(trimethylsilyl)thiazole;chloroformic acid ethyl ester in toluene at 22; for 2.25 h;
Stage #2: with water;sodium carbonate in toluene for 0.5 h;

Steps:

9
Preparation 9Thiazole-2-carboxylic acid ethyl esterTo a mixture of 2-trimethylsilylthiazole (135 g, 858.1 mmol) in toluene (1350 mL) add a solution of ethyl chloroformate (98.4 mL, 1.03 mol) in toluene (1350 mL) over 15 min. Stir the reaction at 22 ⁰C for 2 h. Add the solution over aqueous sodium carbonate 25% (wt/wt) (5 L) and stir for 30 min. Separate the organic layer and re-extract the aqueous layer with methylene chloride (2 x 1 L). Combine the organic layers and evaporate the solvent to provide the title compound (134 g, 99%). ES/MS m/z 158 (M+l)⁺.

References:

ELI LILLY AND COMPANY WO2008/36579, 2008, A1 Location in patent:Page/Page column 26

79265-30-8 Synthesis

79265-30-8
188 suppliers
$22.00/1g

541-41-3
0 suppliers
$19.39/5g

14527-42-5
91 suppliers
$9.00/100mg