Methyl3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate

white to light yellow crystal powder

General procedure: The appropriate 3-amino-2-thenoate 1 (14 mmol) and TsOH·H2O (10.64 g, 56 mmol) were added to a mixture of acetonitrile (100 ml) and water (25 ml). The mixture was heated until a homogeneous solution was obtained, and then cooled in an ice bath with vigorous stirring to obtain a finely dispersed precipitate of the aminium tosylate salt. The solution of NaNO2 (1.10 g, 16 mmol) in water (4 ml) was added in one portion to theobtained suspension. The resulting dark-red solution was added dropwise to the boiled suspension of CuCl (6.93 g, 70 mmol) in acetonitrile (40 ml) under the inert atmosphere.The mixture was boiled for 5 minutes, while nitrogen was observed, after that it was diluted with water (300 ml) and extracted with methylene chloride (3 × 40 ml). The organic layers were combined, dried with K2CO3, passed through a short layer of SiO2, and then concentrated under reduced pressure. The resulting residue of 2 was recrystallized from ethyl acetate : isopropanol (1:1, v/v), except for 2, which was obtained in analytically pure form after the column chromatography.General procedure: NaOH (0.16 g, 4 mmol) in water (1 ml) was added to a stirred suspension of an appropriate 3-aminoester 1 (1 mmol) in i-PrOH (9 ml), and the reaction mixture was stirred and heated at reflux for 4 h. Then, the resulted solution was concentrated to dryness under reduced pressure. The solid residue was dissolved in AcOH (7 ml) or in a mixture of AcOH (7ml) and MeCONMe2 (7ml) in the cases of esters 1c, j, k. Arylhydrazine 2 [2a (0.16 g, 1.5 mmol) / 2b (0.18 g, 1.5 mmol) / 2c (0.23 g, 1.5 mmol)] was added and the reaction mixture was stirred and heated at reflux for 1.5 h. The precipitate was filtered, washed with MeOH (3×4 ml) and dried at 120 C to give product 3 in an analytically pure form.

Molecular Weight:267.73
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:267.0120774
Monoisotopic Mass:267.0120774
Topological Polar Surface Area:80.6
Heavy Atom Count:17
Complexity:282
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes