Isopropanol → 4-Isopropoxy-N-methyl-3-nitrobenzenesulfonamide

HRID 536040노트

반응식

HRID 536040 반응식
[H-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].F[C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH3:18])(=[O:16])=[O:15])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20].CCOC(C)=O>O>[CH3:18][NH:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([O:6][CH:3]([CH3:5])[CH3:4])=[C:9]([N+:19]([O-:21])=[O:20])[CH:10]=1)(=[O:16])=[O:15]

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 84680854-fluoro-N-methyl-3-nitrobenzenesulfonamide

생성물 1

HCID 699352384-Isopropoxy-N-methyl-3-nitrobenzenesulfonamide수율 58%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

NaH (0.440 g, 11 mmol) was added to 20 mL of isopropanol and the resulting mixture stirred at room temperature. After 30 minutes, 4-fluoro-N-methyl-3-nitrobenzenesulfonamide (2.34 g, 10 mmol) was added. The reaction mixture was then stirred at room temperature overnight. The mixture was poured into EtOAc and water. The organic phase was separated, dried over Na2SO4, and concentrated in vacuo to give the crude product. Purification via column chromatography (1:1 petroleum ether/ethyl acetate) afforded N-methyl-4-[(1-methylethyl)oxy]-3-nitrobenzenesulfonamide (1.6 g, 58% yield) as a yellow solid. MS (m/z) 274.7 (M+H+)

후처리

  1. stirringThe reaction mixture was then stirred at room temperature overnight
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customPurification via column chromatography (1:1 petroleum ether/ethyl acetate)

출처 및 근거

ORD 기록
ord-16445e4b802040e1b77f22b45efca9d6
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859571B2

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