Methanesulfonyl chloride → 5-Methanesulfonamidobenzothiophene

HRID 1086857

反応式

HRID 1086857 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(O)C.[Pd]>[CH3:13][S:14]([NH:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)(=[O:16])=[O:15]

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 124140845-Nitro-1-benzothiophene

生成物 1

HCID 149860045-Methanesulfonamidobenzothiophene収率 27.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 5.00 g (0.028 mol) of 5-nitrobenzothiophene (Bordwell, J. Am. Chem. Soc., 77, 5939 (1955)) in 175 mL of ethanol was hydrogenated at 50 psi over 0.5 g of 10% Pd/c for 1.5 hours. The catalyst was removed by filtration, and the solvent was removed under reduced pressure. The residue, 4.39 g, was dissolved in a mixture of 8.4 g of pyridine and 50 mL of methylene chloride. The solution, treated with 3.45 g (0.03 mol) of methanesulfonyl chloride, was stirred overnight at room temperature. The solution was washed with water, dried over MgSO4, filtered, and the solvent removed under reduced pressure to give 1.74 g of crystalline 5-methanesulfonamidobenzothiophene.

後処理

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue, 4.39 g, was dissolved in a mixture of 8.4 g of pyridine and 50 mL of methylene chloride
  4. washThe solution was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-cefa3ae0700e4382a938f2c15691f8bd
出典データセット
uspto-grants-1991_07
特許番号
US05032598

関連ノート

読み込み中…