Triethylamine → (E)-N,N-diallyl-4-(2-(4-bromophenyl)vinylsulfonamido)pyridine-3-sulfonamide
Reaction equation
C(N(CC)CC)C.[CH2:8]([N:11]([CH2:22][CH:23]=[CH2:24])[S:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[NH2:21])(=[O:14])=[O:13])[CH:9]=[CH2:10].[Br:25][C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[S:34](Cl)(=[O:36])=[O:35])=[CH:28][CH:27]=1>N1C=CC=CC=1>[CH2:22]([N:11]([CH2:8][CH:9]=[CH2:10])[S:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[NH:21][S:34](/[CH:33]=[CH:32]/[C:29]1[CH:30]=[CH:31][C:26]([Br:25])=[CH:27][CH:28]=1)(=[O:35])=[O:36])(=[O:14])=[O:13])[CH:23]=[CH2:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Triethylamine (0.440 mL, 3.16 mmol) added was to a solution of N,N-diallyl-4-aminopyridine-3-sulfonamide (0.40 g, 1.58 mmol) in pyridine (10 mL), the mixture was stirred for 5 min and (E)-2-(4-bromophenyl)ethenesulfonyl chloride (0.53 g, 1.89 mmol) was added. After stirring over night the pyridine was evaporated, diluted hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (97:3) as the eluent, gave the title compound in 60% yield.
Workup
- customwas evaporated
- additiondiluted hydrochloric acid was added
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic phase was dried over magnesium sulfate
- customthe solvent was evaporated
- customPurification by column chromatography
Sources & evidence
- ORD record
- ord-1f907b8c63574329bb167839e0a88764
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145380B2
Reaction notes
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