ChemicalBook CAS DataBase List 5-Thiazolecarboxylicacid,2-bromo-4-(1-methylethyl)-,ethylester(9CI)

5-Thiazolecarboxylicacid,2-bromo-4-(1-methylethyl)-,ethylester(9CI) synthesis

3synthesis methods

Product Name:5-Thiazolecarboxylicacid,2-bromo-4-(1-methylethyl)-,ethylester(9CI)
CAS Number:81569-58-6
Molecular formula:C9H12BrNO2S
Molecular Weight:278.17

72850-76-1 Synthesis

2-Amino-4-isopropyl-thiazole-5- carboxylic acid ethyl ester

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5-Thiazolecarboxylicacid,2-bromo-4-(1-methylethyl)-,ethylester(9CI)

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Yield:81569-58-6 90%

Reaction Conditions:

with copper(I) bromide;isopentyl nitrite in acetonitrile at 80; for 3 h;

Steps:

16.2

Step 2 2-Bromo-4-iso^propyl-thiazole-5-carboxylic acid ethyl esterTo a solution of 2-amino-4-isopropyl-thiazole-5-carboxylic acid ethyl ester (4.28 g, 20 mmol) in CH₃CN (30 mL) is added iso-amylnilrite (4.3 mL, 32 mmol) followed by copper bromide (8.9 g, 40 mmol). The reaction mixture is stirred at 80 ⁰C for 3 hours and concentrated under reduced pressure. The residue is partitioned between EtOAc and water. The organic phase is filtered through a Celite pad and the filtrate is concentrated under reduced pressure . The residue is purified by column chromatography (gradient: 0 to 10% EtOAc in hexanes) to give the title product (5 g, 90%). ¹H NMR (CDCl₃) δ 4.33 (q, 2H), 3.95 (m, IH), 1.36 (t, 3H), 1.28 (d, 6H).

References:

WO2007/92751,2007,A2 Location in patent:Page/Page column 18-19

Pentanoic acid, 2-bromo-4-methyl-3-oxo-, ethyl ester

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References

7152-15-0 Synthesis

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References