4-Toluenesulfonyl chloride → HCID 57991620, compound

Participants

Reaction Steps

To a 100 ml eggplant-shaped flask were added 1.00 g (3.37 mmol) 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1, 0.68 g (6.75 mmol) triethylamine and 25 ml THF, added dropwise 1.28 g (6.74 mmol) p-tolylsulfonyl chloride which was dissolved in 5 ml THF. The resulting mixture was stirred at room temperature for 24 hours, filtered, washed with THF, the mother liquid was concentrated under a reduced pressure to a give crude product, which was recrystallized with acetone to obtain a 1.04 g product as a off-white solid in a yield of 51.0%, mp: 182-183 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.45 (6H, s, 2×PhCH3), 3.84 (3H, s, OCH3), 4.26 (2H, s, CH2), 6.92 (2H, d, J=8.68 Hz, ArH), 7.18˜7.36 (9H, m, ArH), 7.46 (2H, d, J=8.68 Hz, ArH), 7.92 (4H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 604.2 (M+, 19), 450.2 (44), 294.2 (78), 91.1 (100); HREI-MS Calcd. for C31H28N2O5S3: 604.1160. found: 604.1165. Anal. Calcd. for C31H28N2O5S3: C, 61.57; H, 4.67; N, 4.63. found: C, 61.71; H, 4.49; N, 4.82.

Provenance & Evidence