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

HRID 1064491

反応式

HRID 1064491 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ffe290f2cf4848bebfcef6d8f4cecd27
出典データセット
uspto-grants-2005_11
特許番号
US06969710B2

関連ノート

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