Triethylamine → Ibrolipim

HRID 1090067

Reaktionsgleichung

Reaktionsgleichung von HRID 1090067
[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.C(N(CC)C1C=CN=CC=1)C.[CH2:29]([O:31][P:32]([CH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)([O:34][CH2:35][CH3:36])=[O:33])[CH3:30]>ClCCl.O>[CH2:35]([O:34][P:32]([CH2:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([NH:1][C:2]2[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=2[C:4]#[N:5])=[O:43])=[CH:45][CH:46]=1)([O:31][CH2:29][CH3:30])=[O:33])[CH3:36]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 4297402-Amino-5-bromobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chlorideHCID 117687514-Diethylaminopyridine

Produkt 1

HCID 131601Ibrolipim

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3.94 Grams (20 mM) of 2-amino-5-bromobenzonitrile, 2.22 g (22 mM) of triethylamine and 0.49 g (4 mM) of 4-diethylaminopyridine were dissolved in 40 ml of anhydrous dichloromethane. To this solution was added dropwise 40 ml of anhydrous dichloromethane solution with 5.81 g (20 mM) of 4-diethoxyphosphinoylmethylbenzoyl chloride at 0° C. with stirring. After the stirring was continued for 10 hours at room temperature, 50 ml of water was added to the reaction mixture, and the whole mixture was extracted with chloroform. The chloroform extracts were dried over anhydrous sodium sulfate and concentrated. Thus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:2). The crude crystals were recrystallized from benzene-n-hexane to yield 2.94 g of 4-diethoxyphosphinoylmethyl-N-(4-bromo-2-cyanophenyl)benzamide as colorless crystals.

Aufarbeitung

  1. extractionthe whole mixture was extracted with chloroform
  2. dry with materialThe chloroform extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThus obtained residue was purified by means of a silica gel column chromatography (eluted with chloroform:ethyl acetate=1:2)
  5. customThe crude crystals were recrystallized from benzene-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-43060edbba47469c855c06a69af44138
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081112

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