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

HRID 41078

反応式

HRID 41078 の反応式
[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]

参加物

6

反応物 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 114473754-(4-Nitrophenyl)-morpholin-3-ON収率 17.6%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ca427a733bc47bd8ae2c708bca74170
出典データセット
uspto-grants-2013_09
特許番号
US08530505B2

関連ノート

読み込み中…