ChemicalBook CAS DataBase List Methyl 2-Aminothiazole-4-carboxylate

Methyl 2-Aminothiazole-4-carboxylate synthesis

7synthesis methods

Product Name:Methyl 2-Aminothiazole-4-carboxylate
CAS Number:118452-04-3
Molecular formula:C5H6N2O2S
Molecular Weight:158.18

A solution of methyl 3-bromo-2-oxo-propanoate (10 g, 51 mmol) and thiourea (4.0 g, 552 mmol) in EtOH (200 mL) was added CuOAc (0.3 g, 2.62 mmol), then stirred at room temperature for 10 h. The mixture was concentrated to give the crude product (16 g). The crude product was basified with NaHC03 to pH=8, then extracted with EtOAc (200 mL x 3). The organic layer was washed with H20 (100 mL) and brine (100 mL), and then dried over anhydrous Na2S04, and then concentrated to give the product Methyl 2-Aminothiazole-4-carboxylate (8.0 g) as a yellow solid.

5398-36-7 Synthesis

Ethyl 2-amino-1,3-thiazole-4-carboxylate

5398-36-7
394 suppliers
$6.00/5g

124-41-4 Synthesis

124-41-4
692 suppliers
$12.00/25g

118452-04-3
264 suppliers
$5.00/1g

Yield:118452-04-3 45%

Reaction Conditions:

in methanol at 0; for 1 h;Cooling with ice;

Steps:

3.2

A mixture of 2-amino-thiazole-4-carboxylic acid ethyl ester (38 g, 221 mmol) in methanol (400 mL) was cooled in an ice bath and to it was added 25% sodium methoxide over 30 minutes. The ice bath was removed after 30 minutes. A few small particles were filtered off and to this yellow solution was added saturated aqueous ammonium chloride and it was concentrated to remove excess methanol. The mixture was adjusted to pH=9.0 with sodium bicarbonate and extracted using 1:1 ether/tetrahydrofuran (3×200 mL). The combined organic extracts were washed with water, dried over sodium sulfate and concentrated to give a pale yellow solid which still contained some solvent. It was taken into hexanes, filtered on a 5.5 cm funnel then dried in vacuo to give 2-amino-thiazole-4-carboxylic acid methyl ester as a pale yellow solid (15.6 g, 45%).

References:

US2006/63814,2006,A1 Location in patent:Page/Page column 28

7425-63-0 Synthesis