Ethanol → HCID 178480159, compound

Participants

Reaction Steps

Compound 36 (124 mg, 0.482 mmol) and anhydrous ethanol (10 mL) were charged to a dry argon purged flask fitted with magnetic stirbar. Thiophene-2-carboximidothioic acid methyl ester hydroiodide (178.5 mg, 0.626 mmol) is added to the flask and the reaction was stirred under argon at ambient temperature for 96 hours. The solution was diluted with diethyl ether (50 mL) resulting in the formation of an off-white precipitate which was collected on a sintered glass funnel and washed with ether. The solid was partitioned between H2O and ethyl acetate and 3M sodium hydroxide solution added to adjust pH to 9. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (2M NH3 in methanol:CH2Cl2, 1:9) to afford a pale yellow residue 37 (100 mg, 56.6%); 1H NMR (DMSO-d6) δ 7.60 (d, 1H, J=3.8 Hz), 7.51 (m, 2H), 7.39-7.34 (2×m, 2H), 7.16-7.13 (m, 1H), 7.06 (dd, 1H, J=3.8, 5.1 Hz), 6.86-6.54 (brs, 2H), 6.37 (d, 1H, J=3.0 Hz), 4.38 (s, 2H), 4.16 (t, 2H, J=7.3 Hz), 2.94-2.87 (m, 1H), 2.16 (s, 3H), 2.11-1.92 (2×m, 3H), 1.89-1.80 (m, 1H), 1.69-1.55 (m, 3H), 1.48-1.36 (m, 1H); ESI-MS (m/z, %): 367 (M+1, 100%).

Provenance & Evidence