6-Methoxy-m-toluenesulfonyl chloride → Benzo[b]thiophene-2sulfonic acid [2-(2-methoxy-5-methylbenzenesulfonylamino)phenyl]-amide

HRID 730220

反応式

HRID 730220 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[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1[S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.N1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1[S:30]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10])(=[O:31])=[O:32]

参加物

5

反応物 2

HCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 86240018Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amide

生成物 1

HCID 11518776Benzo[b]thiophene-2sulfonic acid [2-(2-methoxy-5-methylbenzenesulfonylamino)phenyl]-amide収率 79.8%

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 benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)-amide (1 mmol, prepared as in Example 1) in DCM (2 mL) and pyridine (2 mL), 2-methoxy-5-methylbenzenesulfonyl chloride (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (10 mL). The organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL) and brine (10 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 obtain 390 mg of benzo[b]thiophene-2-sulfonic acid [2-(2-methoxy-5-methylbenzenesulfonylamino)phenyl]-amide. LC: Tr 1.25 min; MS: 489.1 (M+1)+.

後処理

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

出典と根拠

ORDレコード
ord-a1631ad6ce614e76885649047060fa4d
出典データセット
uspto-grants-2009_09
特許番号
US07582673B2

関連ノート

読み込み中…