Water → N-ethyl-N-(5-fluoro-2-nitrophenyl)methanesulfonamide

HRID 346760

반응식

HRID 346760 반응식
[CH2:1]([NH:3][S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].[H-].[Na+].F[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].O>CN(C=O)C>[CH2:1]([N:3]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 679672,4-DifluoronitrobenzeneHCID 5136276N-Ethylmethanesulfonamide

생성물 1

HCID 22272466N-ethyl-N-(5-fluoro-2-nitrophenyl)methanesulfonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

N-ethyl-methanesulfonamide (Mijs et al. J. Chem. Soc. Chem. Com. 1972 p412) (5 g 40.6 mmol) was added to a suspension of sodium hydride (1.9 g, 55% in mineral oil) in anhydrous DMF (100 mL) under nitrogen. The mixture was warmed to 55° C. for one hour and 2,4-difluoronitrobenzene (4.4 mL) was added dropwise. The reaction was stirred at 60° C. overnight, poured into water (500 mL) and the product extracted into CH2Cl2 (5×100 mL). The organic extracts were washed with water, dried over MgSO4 and evaporated to give an oily product. The remaining DMF was removed by trituration with petrol. The crude product was purified by flash chromatography (ethyl acetate:petrol 1:1) to yield the desired product which was recrystallised from ethanol. Yield 3.5 g (33%). Calculated N % 10.68 C % 41.22 S % 12.23 H % 4.23; Found N % 10.68 C % 41.39 S % 12.22 H % 4.17.

후처리

  1. extractionthe product extracted into CH2Cl2 (5×100 mL)
  2. washThe organic extracts were washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto give an oily product
  6. customThe remaining DMF was removed by trituration with petrol
  7. customThe crude product was purified by flash chromatography (ethyl acetate:petrol 1:1)

출처 및 근거

ORD 기록
ord-a4cd6633da1a4f358cd8a1923e7aecb7
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173035B2

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