Methyl 3-amino-4-phenylthiophene-2-carboxylate synthesis
- Product Name:Methyl 3-amino-4-phenylthiophene-2-carboxylate
- CAS Number:82437-64-7
- Molecular formula:C12H11NO2S
- Molecular Weight:233.29
73591-08-9
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82437-64-7
GENERAL STEPS: Sodium methanolate (5 M methanol solution, 3.5 mL, 17.6 mmol) and methyl mercaptoacetate (1.8 mL, 20.1 mmol) were added sequentially to 3-methoxy-2-phenylacrylonitrile (2 g, 12.6 mmol). The reaction mixture was stirred and refluxed at 65 °C overnight. After completion of the reaction, the mixture was filtered using diatomaceous earth and the filter cake was washed with dichloromethane. The crude product was purified by column chromatography (silica gel, n-hexane: ethyl acetate = 5:1) to afford the white solid product methyl 3-amino-4-phenylthiophene-2-carboxylate (1.5 g, 6.6 mmol, 52% yield in two steps). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.49-7.39 (m, 5H), 7.25 (s, 1H), 5.64 (br, 2H), 3.88 (s, 3H).
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Yield:82437-64-7 80%
Reaction Conditions:
with hydrogenchloride;18-crown-6 ether;potassium hydroxide in water;acetonitrile; for 0.333333 h;Thorpe reaction;
References:
Shah [E-Journal of Chemistry,2011,vol. 8,# 1,p. 368 - 372] Location in patent:experimental part
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82437-64-7
53 suppliers
$21.00/100mg