p-Toluenesulfonic acid → 3-biphenyl-4-yl-4-(2-fluorophenyl)-5-isopropyl-4H-1,2,4-triazole

HRID 1797112Notes

Reaction equation

HRID 1797112 reaction equation
CS[C:3](=[N:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14])[CH:4]([CH3:6])[CH3:5].[C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:18]([C:21]([NH:23][NH2:24])=O)=[CH:17][CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O>[C:15]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:18]([C:21]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[F:14])[C:3]([CH:4]([CH3:6])[CH3:5])=[N:24][N:23]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 72718p-PhenylbenzhydrazideHCID 22019263N-(2-Fluorophenyl)-2-methylthiopropionimidate methyl ester

Product 1

HCID 220192343-biphenyl-4-yl-4-(2-fluorophenyl)-5-isopropyl-4H-1,2,4-triazoleYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-Fluorophenyl)-2-methylthiopropionimidate methyl ester (7.84 g) prepared in the Reference Example 1 and biphenyl-4-carboxylic acid hydrazide (5.25 g) were dissolved in N,N-dimethylformamide (50 ml), followed by addition of p-toluenesulfonic acid.monohydrate (941 mg), and stirred at 120° C. for 59 hours. After the reaction solution was cooled to ambient temperature, the resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent:chloroform-chloroform/methanol=100/1 to 50/1 to 20/1), to afford 3-biphenyl-4-yl-4-(2-fluorophenyl)-5-isopropyl-4H-1,2,4-triazole as pale yellow solid (5.98 g, 68%). A part of the product was recrystallized from ethyl acetate, to afford the entitled compound as pale yellow crystal. The physico-chemical values are as follows.

Workup

  1. concentrationthe resulting solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (eluent:chloroform-chloroform/methanol=100/1 to 50/1 to 20/1)

Sources & evidence

ORD record
ord-e78a2968838e42b5bbf748aad6033ba2
Source dataset
uspto-grants-2006_04
Patent number
US07034047B2

Reaction notes

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