p-Fluoronitrobenzene → 4-(4-Nitrophenyl)-morpholin-3-ON

HRID 68466

반응식

HRID 68466 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].[H-].[Na+].[H][H].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>CN1CCCC1=O>[N:1]1([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7]

참가 물질

6

반응물 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 114473754-(4-Nitrophenyl)-morpholin-3-ON수율 17.6%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

2 mol (202 g) of morpholin-3-one (E. Pfeil, U. Harder, Angew. Chem. 79, 1967, 188) are dissolved in 2 l of N-methylpyrrolidone (NMP). Over a period of 2 h, 88 g (2.2 mol) of sodium hydride (60% in paraffin) are then added a little at a time. After the evolution of hydrogen has ceased, 282 g (2 mol) of 4-fluoronitrobenzene are added dropwise with cooling at room temperature, over a period of 1 h, and the reaction mixture is then stirred overnight. At 12 mbar and 76° C., 1.7 l of the liquid volume are then distilled off, the residue is poured into 2 l of water and this mixture is extracted twice with in each case 1 l of ethyl acetate. After washing of the combined organic phases with water, the mixture is dried over sodium sulphate and the solvent is distilled off under reduced pressure. Purification is carried out by silica gel chromatography using hexane/ethyl acetate (1:1) and subsequent crystallization from ethyl acetate. This gives 78 g of product as a colourless to brownish solid, in a yield of 17.6% of theory.

후처리

  1. distillationAt 12 mbar and 76° C., 1.7 l of the liquid volume are then distilled off
  2. additionthe residue is poured into 2 l of water
  3. extractionthis mixture is extracted twice with in each case 1 l of ethyl acetate
  4. washAfter washing of the combined organic phases with water
  5. dry with materialthe mixture is dried over sodium sulphate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customPurification
  8. customhexane/ethyl acetate (1:1) and subsequent crystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-965ed1c7175948cc9794bb3962fe9f51
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822458B2

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