Sulfanilamide → HCID 68632037, compound

Reaction equation

[CH2:1]1[N:8]([CH2:9][CH2:10][N:11]2[CH2:18][C:16](=[O:17])[O:15][C:13](=[O:14])[CH2:12]2)[CH2:7][C:5](=[O:6])[O:4][C:2]1=[O:3].[S:19]([NH2:29])(=[O:28])([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[O:20].[I:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>CN(C=O)C>[C:5]([CH2:7][N:8]([CH2:1][C:2]([NH:35][C:34]1[CH:36]=[CH:37][C:31]([I:30])=[CH:32][CH:33]=1)=[O:3])[CH2:9][CH2:10][N:11]([CH2:12][C:13](=[O:14])[NH:27][C:24]1[CH:23]=[CH:22][C:21]([S:19](=[O:28])(=[O:20])[NH2:29])=[CH:26][CH:25]=1)[CH2:18][C:16]([OH:15])=[O:17])([OH:4])=[O:6]

Participants

Procedure

A solution of EDTA dianhydride (256 mg, 1.0 mmol) and sulfanilamide (172 mg, 1.0 mmol) in DMF (10.0 mL) was stirred at room temperature for 4 h. 4-Iodoaniline (219 mg, 1.0 mmol) was added to the reaction mixture and the resulting reaction mixture was stirred at room temperature for at least 12 hours (overnight). The solvent was evaporated under reduced pressure and purified over AmberChrom™ resin eluting with CH3CN/water to give the title compound (35.4 mg, 5.5%) as a white solid. 1H NMR (400 MHz, DMSO) δ 10.41 (brs, 1H), 10.19 (s, 1H), 7.79 (d, J=8.0 Hz, 2H), 7.73 (d, J=8.0 Hz, 2H), 7.61 (d, J=8.8 Hz, 2H), 7.47 (d, J=8.8 Hz, 2H), 7.24 (s, 2H), 3.50-3.46 (m, 8H), 2.80 (s, 4H); MS (ESI), 648 (M+H)+.