1,1'-Biphenyl, 4'-(bromomethyl)-2-nitro- → 5-n-Butyl-2,4-dihydro-4-[(2'-nitrobiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

HRID 36208

Reaktionsgleichung

Reaktionsgleichung von HRID 36208
[CH2:1]([C:5]1[NH:6][C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[N+:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:35]=[CH:34][C:33]([CH2:36]Br)=[CH:32][CH:31]=1)([O-:23])=[O:22]>>[CH2:1]([C:5]1[N:6]([CH2:36][C:33]2[CH:32]=[CH:31][C:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N+:21]([O-:23])=[O:22])=[CH:35][CH:34]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

3

Edukt 2

HCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-HCID 1355270275-n-Butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Produkt 1

HCID 104809465-n-Butyl-2,4-dihydro-4-[(2'-nitrobiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-oneAusbeute 91 %

Versuchsvorschrift

By the procedure of Example 13, Step A, 5-n-butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 16, Step A) was alkylated with (2'-nitrobiphenyl-4-yl)methyl bromide (from Step B). Flash chromatography of the crude product on silica gel (gradient elution with 0.5-5% MeOH in CH2Cl2) gave a 91% yield of the title compound as a sticky foam; satisfactory purity by TLC in 98:2 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 497 (M+1)+.

Quellen und Nachweise

ORD-Eintrag
ord-f2f1662e807d4ece871809d2e3d42225
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411980

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