Pyridine → 3-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid methyl ester

HRID 2180380ノート

反応式

HRID 2180380 の反応式
[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]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 7515N-MethylanilineHCID 737087423-(3-Chlorosulfonylphenyl)acrylic acid methyl ester

生成物 1

HCID 670195883-[3-(Methylphenylsulfamoyl)phenyl]acrylic acid methyl ester収率 28%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 10% HCl
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. customthe residue was chromatographed on silica gel with chloroform-ethyl acetate (15:1
  7. washThe obtained product was washed with diethyl ether

出典と根拠

ORDレコード
ord-1fe615aa77a04d6da441e7e9aba0cfe4
出典データセット
uspto-grants-2005_05
特許番号
US06888027B2

反応ノート

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