2-Aminothiazole → 4-Iodo-N-(thiazol-2-yl)benzenesulfonamide

반응식

[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH:7]1[C:12]([S:13](Cl)(=[O:15])=[O:14])=[CH:11][CH:10]=[C:9]([I:17])[CH:8]=1.Cl.S1C(N)=NC=N1>N1C=CC=CC=1>[I:17][C:9]1[CH:8]=[CH:7][C:12]([S:13]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)(=[O:15])=[O:14])=[CH:11][CH:10]=1

참가 물질

실험 절차

To a stirring solution of 2-aminothiazole (13.2 g, 132.2 mmol) and pyridine (20 mL) under N2, at 0° C., was added pipsyl chloride (20.0 g, 55.1 mmol). The mixture was stirred at ambient temperature for 17 hours. CH2Cl2/MeOH-2/1 (100 mL) was added. The mixture was filtered and the filtrate was purified via silica gel chromatography using 5% MeOH in CH2Cl2. The solid was triturated with CH2Cl2 to obtain the desired sulfonamide as a white solid (8.4 g, 20.9 mmol, 38% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.83 (s, 1H), 7.94-7.90 (m, 2H), 7.57-7.54 (m, 2H), 7.26 (d, J=4.6 Hz, 1H), 6.86 (d, J=4.6 Hz, 1H).