Toluene → 4'-((2-Butyl-4-oxo-1,3-diazaspiro(4.4)non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrile

HRID 1275806

Reaktionsgleichung

Reaktionsgleichung von HRID 1275806
Cl.[CH2:2]([CH:6]1[NH:10][C:9](=[O:11])[C:8]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[NH:7]1)[CH2:3][CH2:4][CH3:5].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1.C1(C)C=CC=CC=1.[OH-].[Na+]>[Cl-].C[N+](CCCC)(CCCC)CCCC.O>[CH2:2]([C:6]1[N:10]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:22][CH:23]=2)[C:9](=[O:11])[C:8]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[N:7]=1)[CH2:3][CH2:4][CH3:5]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 221178832-Butyl-1,3-diazaspiro[4.4]nonan-4-one hydrochloride

Produkt 1

HCID 98431164'-((2-Butyl-4-oxo-1,3-diazaspiro(4.4)non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrileAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 91822Tributylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 0.231 g (1.0 mmol) of 2-butyl-1,3-diazaspiro [4.4]nonan-4-one, hydrochloride, 0.272 g (1.0 mmol) of 4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile, 24.4 μL (0.075 mmol) of 75% aqueous solution of methyl-tributylammonium chloride, 2.0 mL of toluene and 2.0 mL of 50% aqueous solution of sodium hydroxide was vigorously stirred at room temperature for 2.2 hours. Then the reaction mixture was diluted with 2 mL of water and the two phases separated. The organic phase was extracted twice with 2 mL of water, evaporated under vacuum to give 0.33 g (85.7%) of the title compound.

Aufarbeitung

  1. customthe two phases separated
  2. extractionThe organic phase was extracted twice with 2 mL of water
  3. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5e5224e00cd642edb0050072f3bdc298
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162922

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