m-Chloroperbenzoic acid → N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-(1-oxidopyridin-4-yl)-1H-pyrazol-3-yl]aniline

HRID 45836Notes

Reaction equation

HRID 45836 reaction equation
[C:1]1([C:7]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[C:19]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[CH:18][N:17]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[N:16]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:49])C=1>C(COC)OC>[C:35]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[C:19]([C:20]4[CH:25]=[CH:24][N+:23]([O-:49])=[CH:22][CH:21]=4)=[CH:18][N:17]([CH2:26][C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)[N:16]=3)[CH:10]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86654334N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]aniline

Product 1

HCID 86654335N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-(1-oxidopyridin-4-yl)-1H-pyrazol-3-yl]anilineYield 78.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

100 mg (0.19 mmol) of N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]aniline were reacted with 36 mg (0.21 mmol) of m-chloroperbenzoic acid in 4 ml of dimethoxyethane. The solution was stirred at room temperature overnight. The reaction mixture was partitioned between dichloromethane and aqueous NaHCO3, the organic layer dried over Na2SO4 and the solvent removed under reduced pressure. The residue was triturated with diethylether and collected by filtration giving 80 mg (78%) of the title compound.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and aqueous NaHCO3
  2. dry with materialthe organic layer dried over Na2SO4
  3. customthe solvent removed under reduced pressure
  4. customThe residue was triturated with diethylether
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-718810ec3aa14d1bb67e027b67dd7c7c
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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