m-Chloroperbenzoic acid → HCID 66919237, compound

HRID 1469334Notes

Reaction equation

HRID 1469334 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][C:28]2([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:12][CH2:13][C:14]1[N:15]([CH2:27][C:28]2([OH:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:19]([O-:6])=[CH:18][C:17]=2[N:26]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57515598HCID 57515598, compound

Product 1

HCID 66919237HCID 66919237, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (8.37 g of 70% pure material, 34 mmol) was added to a suspension of 1-{[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanol (8.0 g, 24 mmol) in chloroform (100 mL), and the reaction was stirred at room temperature for four hours. Saturated aqueous sodium bicarbonate (100 mL) was added, and the mixture was stirred for 15 minutes. A precipitate formed and was isolated by filtration to provide 1-{[2-(chloromethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanol as a white solid.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customA precipitate formed
  3. customwas isolated by filtration

Sources & evidence

ORD record
ord-f0806727d103430b80834b6c02fd0b19
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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