Pyridine → 3-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:7]=1.[CH3:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([S:12](=[O:14])(=[O:13])[N:18]([CH3:17])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1Participants
Procedure
A solution of 3-(3-chlorosulfonylphenyl)acrylic acid methyl ester (3) (0.440 g, 1.68 mmol) in dichloromethane (2 ml) was added to a mixture of N-methylaniline (0.364 g, 3.40 mmol) and pyridine (0.5 ml), and the resultant solution was stirred at 50° C. for one hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 10% HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with chloroform-ethyl acetate (15:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.155 g, 28%). 1H NMR (CDCl3, HMDSO), δ: 3.12 (3H, s); 3.74 (3H, s); 6.34 (1H, d, J=16.0 Hz); 6.97–7.74 (10H, m).
Workup
- customThe reaction mixture was evaporated
- customthe residue was partitioned between ethyl acetate and 10% HCl
- washThe organic layer was washed successively with water, saturated NaCl
- dry with materialdried (Na2SO4)
- customThe solvent was removed
- customthe residue was chromatographed on silica gel with chloroform-ethyl acetate (15:1
- washThe obtained product was washed with diethyl ether
Sources & evidence
- ORD record
- ord-83d6665c4f4d47a38bc3e2039f6a9ca2
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07183298B2
Reaction notes
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