[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide → 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

HRID 36260Notes

Reaction equation

HRID 36260 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:20]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][CH:35]=1)(=[O:27])=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[CH2:1]([C:5]1[N:6]([CH2:40][C:37]2[CH:38]=[CH:39][C:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[S:25](=[O:27])(=[O:26])[NH:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[CH:35][CH:36]=2)[C:7](=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromideHCID 135720085HCID 135720085, compound

Product 1

HCID 199393815-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-2,4-dihydro-2-(3-nitrophenyl)-3H-1,2,4-triazol-3-oneYield 74%

Procedure

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)+.

Sources & evidence

ORD record
ord-3470d42b6c3144d9a7b58cd4a401fa2f
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

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