Chemical Properties
white to light yellow crystal powder
Uses
Methyl 2-aminothiophene-3-carboxylate may be used to prepare 3-thiaisatoic anhydride via hydrolysis, followed by the reaction with phosgene.
Uses
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.
Definition
ChEBI: Methyl 2-aminothiophene-3-carboxylate is a thiophenecarboxylic acid.
Synthesis
To two 20 mL microwave reaction tubes were added 1,4-dithio-2,5-diol (2.0 g, 13.1 mmol, 1.0 eq.) and methanol (10.5 mL), respectively, and the reaction tubes were sealed. Methyl cyanoacetate (2.32 mL, 26.3 mmol, 2.0 eq.), triethylamine (1.28 mL, 9.20 mmol, 0.7 eq.), and N,N-dimethylformamide (3 drops) were added sequentially through the septum to each reaction tube. The reaction mixture was placed in a microwave reactor and the reaction was heated at 50 °C for 3 min. Upon completion of the reaction, the reaction solutions in the two tubes were combined and left at room temperature to allow the product to precipitate. The precipitate was collected by filtration and washed with cold methanol to afford methyl 2-aminothiophene-3-carboxylate (16as) as a white solid (3.88 g, 24.7 mmol, 94% yield).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 1947 - 1953
[2] Patent: WO2015/959, 2015, A1. Location in patent: Page/Page column 47
[3] Tetrahedron Letters, 2007, vol. 48, # 30, p. 5261 - 5264
[4] Tetrahedron, 2012, vol. 68, # 45, p. 9226 - 9233
[5] Patent: WO2005/63734, 2005, A2. Location in patent: Page/Page column 60-61
