Pyridine → N-Benzyl-N-[3-(2-oxo-imidazolidin-1-yl)-phenyl]-benzenesulfonamide
Reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH2:18][NH:17][C:16]2=[O:20])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:19][CH2:18][NH:17][C:16]2=[O:20])[CH:10]=1)[S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:29])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Procedure
A solution of 1-(3-benzylamino-phenyl)-imidazolidin-2-one (25 mg, 0.1 mmol), benzenesulphonyl chloride (39 μl, 31 mmol) and pyridine (27 μl, 34 mmol) in dry dichloromethane (1 ml) was heated to reflux for 15 hrs. The reaction mixture was then cooled to room temperature, quenched with water (10 ml) and extracted with dichloromethane (3×7 ml). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo. The crude residue was purified by preparative TLC (eluent 1:1 ethyl acetate:dichloromethane) to afford the title compound as a off white solid (9 mg, 24%). HPLC retention time 8.8 mins. Mass spectrum (ES+) m/z 425 (M+NH4).
Workup
- temperatureto reflux for 15 hrs
- customquenched with water (10 ml)
- extractionextracted with dichloromethane (3×7 ml)
- dry with materialdried (magnesium sulphate)
- concentrationconcentrated in vacuo
- customThe crude residue was purified by preparative TLC (eluent 1:1 ethyl acetate:dichloromethane)
Sources & evidence
- ORD record
- ord-bd628d5117d048588d53e99d988a9408
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372840B2
Reaction notes
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