N-(2-aminophenyl)-4-chlorobenzenesulfonamide → Benzofuran-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide

HRID 730215ノート

反応式

HRID 730215 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH:21]=[C:20]1[S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl.N1C=CC=CC=1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([S:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][S:28]([C:20]2[O:19][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH:21]=2)(=[O:29])=[O:30])(=[O:11])=[O:10])=[CH:17][CH:16]=1

参加物

5

反応物 2

HCID 241359N-(2-aminophenyl)-4-chlorobenzenesulfonamideHCID 27951721-Benzofuran-2-sulfonyl chloride

生成物 1

HCID 11626794Benzofuran-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide収率 39.7%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N-(2-aminophenyl)-4-chlorobenzenesulfonamide (0.5 mmol, prepared as in Example 11) in DCM (1 mL) and pyridine (1 mL), benzofuran-2-sulfonyl chloride (0.55 mmol), prepared as above, was added at RT and the reaction mixture was then allowed to stir at RT overnight or until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with DCM (5 mL). The organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL) and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to afford 92 mg benzofuran-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide. LC: Tr 1.13 min, MS: 464.0 (M+1)+.

後処理

  1. additionwas added at RT
  2. washThe organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL) and brine (5 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customwas purified by flash column chromatography
  7. washeluting with DCM/EtOAc

出典と根拠

ORDレコード
ord-a53d164d5b274e2cae64dbc418cb38d9
出典データセット
uspto-grants-2009_09
特許番号
US07582673B2

反応ノート

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