4-Chloro-3-nitrobenzenesulfonamide → 3-Nitro-4-[2-(3-oxo-piperazin-1-yl)-ethylamino]-benzenesulfonamide
Reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][C:6](=[O:10])[CH2:5]1.C(N(CC)CC)C.O1CCOCC1.Cl[C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][C:26]=1[N+:35]([O-:37])=[O:36]>O.CN(C)C(=O)C>[N+:35]([C:26]1[CH:27]=[C:28]([S:31]([NH2:34])(=[O:32])=[O:33])[CH:29]=[CH:30][C:25]=1[NH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][C:6](=[O:10])[CH2:5]1)([O-:37])=[O:36]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
4-(2-Amino-ethyl)-piperazin-2-one (5.51 g) and triethylamine (9.07 mL, 6.59 g) were added to 1,4-dioxane (100 mL), N,N-dimethylacetamide (20 mL), and water (10 mL) and mixed until dissolved. 4-Chloro-3-nitrobenzenesulfonamide (7.00 g) was added, and the mixture was heated to 90° C. for 16 hours. The mixture was cooled and the solvent was removed under vacuum. The crude material was purified by recrystallization from 20% methanol in dichloromethane with subsequent washing of the recrystallized solid with 10% methanol in dichloromethane followed by washing with 100% dichloromethane.
Workup
- additionmixed
- dissolutionuntil dissolved
- temperatureThe mixture was cooled
- customthe solvent was removed under vacuum
- customThe crude material was purified by recrystallization from 20% methanol in dichloromethane
- washwith subsequent washing of the recrystallized solid with 10% methanol in dichloromethane
- washby washing with 100% dichloromethane
Sources & evidence
- ORD record
- ord-a97d0d2e38f64d6f979ca7ec9378b804
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563735B2
Reaction notes
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