Water → Ibrolipim

HRID 650502

Reaktionsgleichung

Reaktionsgleichung von HRID 650502
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[CH2:18]([O:20][P:21]([CH2:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([O:23][CH2:24][CH3:25])=[O:22])[CH3:19].O>CN(C)C1C=CN=CC=1.ClCCl>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C:31]([C:30]2[CH:34]=[CH:35][C:27]([CH2:26][P:21](=[O:22])([O:20][CH2:18][CH3:19])[O:23][CH2:24][CH3:25])=[CH:28][CH:29]=2)=[O:32])=[C:3]([C:4]#[N:5])[CH:6]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 4297402-Amino-5-bromobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chloride

Produkt 1

HCID 131601IbrolipimAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3.94 Grams (20 millimoles) of 2-amino-5-bromo-benzonitrile, 2.22 g (22 millimoles) of triethylamine and 0.49 g (4 millimoles) of 4-dimethylaminopyridine were dissolved in 40 ml of dry dichloromethane, under ice-cooling there was added dropwise slowly 40 ml of dry dichloromethane solution of 5.81 g (20 millimoles) of 4-diethoxyphosphorylmethylbenzoyl chloride with stirring. The reaction was carried out at room temperature for 10 hours, to this reaction mixture was added 50 ml of water, then extracted with chloroform and the organic layer was dried over anhydrous sodium sulfate, next the solvent was removed by distillation under reduced pressure. Thus obtained residue was refined by means of a silica gel column chromatography (eluted with chloroform: ethyl acetate=1:2), recrystallized from benzen-n-hexane, there was obtained 2.94 g of diethyl 4-[N-(4-bromo-2-cyanophenyl)carbamoyl]benzylphosphonate as colorless crystals.

Aufarbeitung

  1. temperaturecooling there
  2. extractionextracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate, next the solvent
  4. customwas removed by distillation under reduced pressure
  5. washThus obtained residue was refined by means of a silica gel column chromatography (eluted with chloroform: ethyl acetate=1:2)
  6. customrecrystallized from benzen-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3e858a521f0046a8b3e02947674c4abf
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274571B1

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