Реакция #64538

ord-3470d42b6c3144d9a7b58cd4a401fa2f

Уравнение реакции

CCCCc1nn(-c2cccc([N+](=O)[O-])c2)c(=O)[nH]1
5-n-butyl-2,4-dihydro-2-(3-nitrophenyl)-3H-1,2,4-triazol-3-one
CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(CBr)cc1
[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl bromide
→
CCCCc1nn(-c2cccc([N+](=O)[O-])c2)c(=O)n1Cc1ccc(-c2ccccc2S(=O)(=O)NC(C)(C)C)cc1
title compound
Выход 74.0%
CCCCc1nn(-c2cccc([N+](=O)[O-])c2)c(=O)n1Cc1ccc(-c2ccccc2S(=O)(=O)NC(C)(C)C)cc1
5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-2-(3-nitrophenyl)-3H-1,2,4-triazol-3-one
Выход 74.0%

Реактанты

CCCCc1nn(-c2cccc([N+](=O)[O-])c2)c(=O)[nH]1
5-n-butyl-2,4-dihydro-2-(3-nitrophenyl)-3H-1,2,4-triazol-3-one
CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(CBr)cc1
[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl bromide

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

By the procedure of Example 13, Step A, 5-n-butyl-2,4-dihydro-2-(3-nitrophenyl)-3H-1,2,4-triazol-3-one (from Step A) was alkylated with [2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl bromide (from Example 12, Step D). Flash chromatography of the crude product on silica gel (gradient elution with 0.5-1.0% MeOH in CH2Cl2) gave a 74% yield of the title compound as an off-white solid, mp 164°-165° C., homogeneous by TLC (19:1 CH2Cl2 --MeOH), mass spectrum (FAB) m/e 564 (M+1)+.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05411980uspto-grants-1995_05