p-Xylyl bromide → 5-n-Butyl-2,4-dihydro-2-(4-methylbenzyl)-4-[(2'-cyanobiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-one

HRID 36181

Reaktionsgleichung

Reaktionsgleichung von HRID 36181
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:7](=[O:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1.[H-].[Na+]>>[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:7](=[O:10])[N:8]([CH2:26][C:27]2[CH:34]=[CH:33][C:30]([CH3:31])=[CH:29][CH:28]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 3

HCID 7721p-Xylyl bromideHCID 24758Sodium hydrideHCID 149510524'-[(3-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)methyl]biphenyl-2-carbonitrile

Produkt 1

HCID 199393955-n-Butyl-2,4-dihydro-2-(4-methylbenzyl)-4-[(2'-cyanobiphenyl-4-yl)methyl]-3H-1,2,4-triazol-3-oneAusbeute 76 %

Versuchsvorschrift

The alkylation of 5-n-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one with 4-methylbenzyl bromide was carried out as described in Example 3, Step A, except that no excess sodium hydride was used. After work-up, flash chromatography of the crude product on silica gel (eluting with 0.6% methanol in CH2Cl2) provided a 76% yield of the title compound as a clear oil, homogeneous by TLC (98:2 CH2Cl2 --MeOH), mass spectrum (FAB) m/e 437 (M+1)+.

Quellen und Nachweise

ORD-Eintrag
ord-7add0288a72b49038c85dfb38b0c0104
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411980

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