Water → HCID 66637332, compound

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH3:10])[CH:5]=[CH:6][C:7]=1[NH2:8].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1.O>C1COCC1.C(Cl)Cl>[CH3:17][C:14]([S:12]([NH:11][CH:9]([C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:23](=[O:24])[NH:1][C:2]=2[CH:3]=1)[CH3:10])=[O:13])([CH3:16])[CH3:15]

Participants

Procedure

A mixture of N-[1-(3,4-diaminophenyl)ethyl]-2-methylpropane-2-sulfinamide and CDI (569 mg, 3.51 mmol) in THF-DCM (10 ml-10 ml) was refluxed for 6 hours. After cooling to the room temperture, water (10 mL) was added to the mixture. The mixture was extracted with EtOAc (150 ml) and organic layer was washed with brine (30 ml), dried over sodium sulfate and concentrated. The residue was recrystallized from EtOAc to afford 430 mg (65%) of the title compound as a pale brown solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.11 (9H, s), 1.38 (3H, d, J=7.3 Hz), 4.37-4.28 (1H, m), 5.53 (1H, d, J=6.6 Hz), 6.84 (1H, d, J=7.3 Hz), 6.93 (1H, d, J=8.1 Hz), 6.99 (1H, s), 10.54 (1H, br.s), 10.60 (1H, br.s). MS (ESI) m/z 282 (M+H)+, 280 (M−H)−.