Methanesulfonyl chloride → 5-Methanesulfonamidobenzothiophene

HRID 1086857

반응식

HRID 1086857 반응식
[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]

참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 124140845-Nitro-1-benzothiophene

생성물 1

HCID 149860045-Methanesulfonamidobenzothiophene수율 27.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cefa3ae0700e4382a938f2c15691f8bd
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05032598

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