Acetic Acid → HCID 10759629, compound

Participants

Reaction Steps

1N sodium hydroxide solution (6 mL, 6 mmol) was added to a solution containing the 4-toluenesulfonamide (1 g, 5.85 mmol) in acetone (25 mL). After stirring at room temperature for 30 min, the 4-chlorophenyl isothiocyanate (1.0 mmol) was added. After refluxing for 4 h, the mixture was cooled to room temperature and neutralized with 1N acetic acid solution to pH 5. The mixture was allowed to stir at room temperature for 30 min before adding water (45 mL) to produce a white precipitate which was collected by filtration. After the solid was dried in the oven, it was recrystallized to give 0.45 g (22.6%) of N-[(4-methylphenyl)sulfonyl]-N'-(4-chlorophenyl)thiourea. To an aqueous solution (50 mL) of sulfonylthiourea (1.2 g, 3.67 mmol), 1N sodium hydroxide solution (4 mL) was added and stirred for 2 minutes, followed by addition of methyl iodide (4.04 mmol). The reaction mixture was stirred at room temperature for 20 minutes, and neutralized with 1N acetic acid (4 mL). The resulting mixture was extracted with chloroform to give 1.06 g (85%) of N-[(4-methylphenyl)sulfonyl]-N'-(4-chlorophenyl)-S-methylpseudothiourea. The S-methyl pseudourea (0.99 g, 2.8 mmol) was added to a stirred solution of hydroxylamine hydrochloride (8.4 mmol) and triethylamine (1.2 mL, 8.4 mmol) in chloroform (50 mL). The solution was refluxed for 48 h and the solvent was removed by evaporation to produce a solid residue. Ether (20 mL) was added to the residue and the white precipitate was collected by filtration. The solid was then heated with toluene and the undissolved solid was removed by filtration. The filtrate was again evaporated to obtain a solid which was subsequently recrystallized from methanol to yield the target compound (0.12 g, 12.7%); mp: 201-203° C.; MS m/z 294 (M+ -32); 1H NMR (300 MHz, DMSO-d6) d 2.36 (s, 3H, CH3), 7.31-7.36 (m, 4H, ArH), 7.45 (d, J=8.8 Hz, 2H, ArH), 7.71 (d, J=8.1 Hz, 2H, ArH), 9.40 (s, 1H, NH), 9.69 (br s, 2H, NH & OH); 13C NMR (100 MHz, DMSO-d6) d 20.9, 124.7, 125.9, 128.2, 128.3, 129.1, 136.2, 140.6, 141.6, 154.0. Analysis for C14H14ClN3O3S (339.8): theory: C, 49.49; H, 4.15; N, 12.37. Found: C, 49.67; H, 4.16; N, 12.47.

Provenance & Evidence