Ethanol → Benzenesulfonamide, 4-amino-N-[2-(4-morpholinyl)ethyl]-
Reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)C.[Cl-].[NH4+]>[Fe].O>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([S:10]([NH:9][CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)(=[O:12])=[O:11])=[CH:18][CH:17]=1Participants
Procedure
N-(2-Morpholin-4-yl-ethyl)-4-nitro-benzenesulfonamide (0.14 g, 0.45 mmol) was suspended in a 5:1 mixture of ethanol and water (3 ml). To this solution was added iron powder (0.13 g, 2.25 mmol) followed by saturated ammonium chloride solution (0.1 ml) and the mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was filtered through a pad of celite, the celite was washed with ethanol (10 ml) and ethyl acetate (50 ml) and the solution was concentrated under vacuum. The resulting residue was partitioned between DCM (50 ml) and water (20 ml), the organic layer was separated, dried with MgSO4, filtered and concentrated to afford the title compound (0.1 g, 78% yield) as a brown solid. Tr=0.35 min, m/z (ES+) (M+H)+ 285.
Workup
- filtrationAfter this time, the reaction mixture was filtered through a pad of celite
- washthe celite was washed with ethanol (10 ml) and ethyl acetate (50 ml)
- concentrationthe solution was concentrated under vacuum
- customThe resulting residue was partitioned between DCM (50 ml) and water (20 ml)
- customthe organic layer was separated
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4ac684ae0b794e45a27c19eac27c0c9e
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946197B2
Reaction notes
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