Methyl thiophene-2-carbimidothioate hydroiodide → HCID 178464027, compound

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Reaction Steps

Compound 9 (75 mg, 0.172 mmol) was dissolved in anhydrous ethanol (5 mL) in a dry argon purged flask. Palladium, 10wt % on activated carbon (18.3 mg, 0.0172 mmol) is quickly added and the atmosphere from the flask evacuated by vacuum pump and replaced with hydrogen from a balloon. The atmosphere is evacuated from the flask and replaced with hydrogen twice more and the mixture stirred under a hydrogen atmosphere at room temperature. After 3 hours, thin layer chromatography (2M NH3 in MeOH:CH2Cl2, 2.5:97.5) shows complete conversion to 10, which is utilized without isolation. The mixture is filtered through a pad of celite to remove insolubles, the pad washed with anhydrous ethanol (5 mL) and the ethanolic solution of the amine 10 is charged to a small, argon purged flask fitted with a magnetic stirbar. Thiophene-2-carboximidothioic acid methyl ester hydroiodide (63.8 mg, 0.224 mmol) is added to the flask and the reaction was stirred under argon at ambient temperature for 45 hours. The solution was diluted with diethyl ether (100 ml) and cooled in an ice bath. No precipitate formed thus the solvent was evaporated. The residue was purified using silica gel column chromatography (2M NH3 in MeOH:CH2Cl2, 2.5:97.5 to 5:95) to afford a pale yellow residue 11 (47 mg, 53.0%). 1H NMR (MeOD) δ 0.98 (t, 6H, J=7.1 Hz), 2.47-2.56 (2×m, 6H), 4.13 (t, 2H, J=7.1 Hz), 4.24 (s, 2H), 6.24 (s, 1H), 6.84 (dd, 1H, J=8.4, 1.6 Hz), 7.09-7.13 (m, 2H), 7.17-7.24 (m, 2H), 7.33-7.39 (m, 3H), 7.56 (d, 1H, J=5.2 Hz), 7.64 (d, 1H, J=3.7 Hz); ESI-MS (m/z, %): 515 (MH+, 100%).

Provenance & Evidence