2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER

The sulfur powder (960.0mg, 30.0mmol)In a single mouth bottle, Add DMF 5 mL, Were successively added methyl cyanoacetate (3.39g, 30.0mmol), Morpholine (1.48 g, 17.0 mmol), The reaction solution was dark brown, Propionaldehyde (1.74 g, 30.0 mmol) was added, 50 ° C overnight.After completion of the reaction, the mixture was cooled to room temperature, Add appropriate amount of water, Ethyl acetate was extracted three times, The combined organic phases were washed with saturated brine, Dried over anhydrous magnesium sulfate, The crude product was distilled under reduced pressure.Separation and purification by column chromatography, To give a pale yellow solid.Yield: 73.6percentGeneral procedure: A solution of aliphatic carbonyl compound 1 (2 mmol), activatednitrile (2 mol), elemental sulfur (2 mmol) and triethylamine(2 mmol) in MeOH (15 ml) was heated at reflux temperature for12 h under argon atmosphere. The MeOH was evaporated underreduced pressure and the residue was extracted with dichloromethane(3 50ml). The combined organic phases were washedwith a saturated solution of NaHCO3, dried over magnesium sulfateand the solvent was evaporated under reduced pressure. Purificationby column chromatography (silica, eluent CH2Cl2) afforded 3 asan off-white solid or a semi-solid.

Molecular Weight:171.22
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:171.03539970
Monoisotopic Mass:171.03539970
Topological Polar Surface Area:80.6
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes