Water → N-(2'-Cyanobiphenyl-4-yl)methyl-N-(2-methoxy-6-nitrophenyl)valeramide

HRID 1655469

Reaktionsgleichung

Reaktionsgleichung von HRID 1655469
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[NH:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17].[H-].[Na+].[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1)#[N:22].O>CN(C=O)C>[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:30]=[CH:31][C:32]([CH2:33][N:12]([C:4]2[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:35][CH:36]=1)#[N:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 19792196N-(2-Methoxy-6-nitrophenyl)valeroamide

Produkt 1

HCID 19792111N-(2'-Cyanobiphenyl-4-yl)methyl-N-(2-methoxy-6-nitrophenyl)valeramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(2-methoxy-6-nitrophenyl)valeramide (3.2 g) in DMF (15 ml) was added, under ice-cooling, sodium hydride (60% oil, 0.61 g). The mixture was stirred for 20 minutes and then there was added 4-(2-cyanophenyl)benzyl bromide (3.5 g), followed by stirring for one hour at room temperature. To the reaction mixture was added water, which was extracted with ethyl acetate. The organic layer was washed with water and dried. The solvent was distilled off, and the residue was purified by column chromatography on silica gel to give a yellow oil (5.8 g, quantitatively).

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring for one hour at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography on silica gel
  8. customto give a yellow oil (5.8 g

Quellen und Nachweise

ORD-Eintrag
ord-f2926a91d7cf479eb930fde0a02b6438
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250554

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