Water → 4-(1,1-Dioxo-5-methyl-1,2,5-thiadiazolidine-2-yl)nitrobenzene
Reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][NH:4][S:3]1(=[O:8])=[O:7].[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.O>CN(C)C=O>[O:7]=[S:3]1(=[O:8])[N:2]([CH3:1])[CH2:6][CH2:5][N:4]1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1Participants
Procedure
To a solution of 2-methyl-1,2,5-thiadiazolidine-1,1-dioxide (2.02 g, 14.8 mmol) in anhydrous dimethylformamide (30 ml) was added sodium hydride (60% dispersion in oil; 0.59 g) and the mixture was stirred at room temperature under nitrogen for 40 minutes. A solution of 1-fluoro-4-nitrobenzene (2.09 g, 14.8 mmol) in anhydrous dimethylformamide (15 ml) was added to the above solution and the mixture was refluxed for 1 hour. Water (200 ml) was added and products were extracted with ethyl acetate (2×150 ml), dried (MgSO4) and concentrated to an orange solid. Crystallisation from ethyl acetate (150 ml) afforded 2.61 g (68.7%) of the title compound as a pale orange solid; mp 155°-163° C.; δH (250 MHz, DMSO-d6) 8.29 (2H, d, J=9.3 Hz, Ar--H), 7.34 (2H, d, J=9.3 Hz, Ar--H), 4.00 (2H, t, J=6.4 Hz, --CH2 --), 3.57 (2H, t, J=6.4 Hz, --CH2 --), 2.78 (3H, s, --CH3); m/z (EI) 257 (M+).
Workup
- temperaturethe mixture was refluxed for 1 hour
- extractionproducts were extracted with ethyl acetate (2×150 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated to an orange solid
- customCrystallisation from ethyl acetate (150 ml)
Sources & evidence
- ORD record
- ord-de167a242cb9403e8021faed60df5081
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194440
Reaction notes
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