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3-Nitrobenzamide → 1-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

HRID 1588032
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HRID 1588032 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH2:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][S:16]([CH3:15])(=[O:18])=[O:17])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]
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참가 물질

6

반응물 3

HCID 125763-NitrobenzamideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chloride

생성물 1

HCID 196035271-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-nitrophenylcarboxamide (2 g) in 150 ml of dry tetrahydrofuran was cooled to 0° C. and treated with 609 mg of sodium hydride (60% oil dispersion). The reaction mixture was stirred for 20 minutes and then methanesulfonylchloride (1.18 ml) was introduced dropwise via syringe. After 5 minutes the reaction mixture became homogeneous and was warmed to room temperature and stirred overnight. The reaction mixture was diluted with 300 ml of ethyl acetate and was washed with brine. The organic extracts were dried, concentrated in vacuo, and the residue was chromatographed on silica gel (ethyl acetate then chloroform-methanol, 95:5 v/v) to yield 1.6 g of the title compound in pure form.

후처리

  1. waitAfter 5 minutes the reaction mixture became homogeneous
  2. stirringstirred overnight
  3. washwas washed with brine
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel (ethyl acetate

출처 및 근거

ORD 기록
ord-17ff4023f4b14d038157070b4c950e28
출처 데이터셋
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05220018

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