Pyridine → N-(3-bromo-4-methylphenyl)-N-(2,2-diethoxyethyl)benzenesulfonamide
Reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([NH:19][CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])[CH:15]=[CH:16][C:17]=1[CH3:18].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[Br:11][C:12]1[CH:13]=[C:14]([N:19]([CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])[S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:15]=[CH:16][C:17]=1[CH3:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen stream, benzenesulfonyl chloride (3.12 mL g, 24.48 mmol) was added dropwise under ice cooling to a mixture of (3-bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine (4.91 g, 16.25 mmol), pyridine (10.1 mL, 124.88 mmol) and dichloromethane (41 mL), and the resultant mixture was then stirred at the same temperature for 1 hour. After stirring at room temperature for 2 hours, the reaction mixture was added to saturated aqueous sodium hydrogen carbonate. The resultant mixture was extracted with dichloromethane. The organic layer was washed with 5% aqueous hydrochloric acid and dried (anhydrous potassium carbonate). Solvent was then removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:4)), to thereby obtain the titled compound (5.94 g, 83%).
Workup
- extractionThe resultant mixture was extracted with dichloromethane
- washThe organic layer was washed with 5% aqueous hydrochloric acid
- dry with materialdried (anhydrous potassium carbonate)
- customSolvent was then removed by distillation under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:4))
Sources & evidence
- ORD record
- ord-d6bbd0b0e5724ba989f8c2ce694e84a4
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207134B2
Reaction notes
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