Sodium p-toluenesulfinate → Methyl 4-(4-{[(4-Methylphenyl)sulfonyl]methyl}-1,3-thiazol-2-yl)benzoate

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Reaction Steps

Reaction of chloride 51 (402 mg, 1.5 mmol) and sodium 4-methylbenzenesulfinate (294 mg, 1.7 mmol) in dry DMF (10 mL) gave benzoate 52 (446 mg, 77%) as a white powder: mp (EtOAc) 160-161° C.; 1H NMR (CDCl3) δ 8.05 (ddd, J=8.6, 1.9, 1.7 Hz, 2H, H-2, H-6), 7.77 (ddd, J=8.6, 1.9, 1.7 Hz, 2H, H-3, H-5), 7.64 (ddd, J=8.3, 1.9, 1.7 Hz, 2H, H-2″, H-6″), 7.42 (s, 1H, H-5′), 7.27 (br d, J=8.3 Hz, 2H, H-3″, H-5″), 4.60 (s, 2H, CH2SO2), 3.94 (s, 3H, OCH3), 2.41 (s, 3H, CH3); MS m/z 388.6 (MH+, 100%). Anal. calcd for C19H17NO4S2: C, 58.90; H, 4.42; N, 3.61. Found: C, 58.83; H, 4.33; N, 3.55%.

Provenance & Evidence