m-Chloroperbenzoic acid → HCID 54239562, compound

HRID 1198850Notes

Reaction equation

HRID 1198850 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[CH3:12][O:13][C:14]([C:16]1[N:20]([CH:21]2C3C(=CC=CC=3)C=[CH:23][C:22]2([CH3:32])[CH3:31])[CH:19]=[N:18][CH:17]=1)=[O:15]>C(Cl)Cl>[CH3:12][O:13][C:14]([C:16]1[N:20]([CH:21]2[C:3]3[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=3)[CH:8]3[O:10][CH:23]3[C:22]2([CH3:32])[CH3:31])[CH:19]=[N:18][CH:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54456308HCID 54456308, compound

Product 1

HCID 54239562HCID 54239562, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.4 g of 55% 3-chloroperbenzoic acid are added to a solution of 8.5 g of 1-(1,2-dihydro-2,2-dimethylnaphthalen-1-yl)-5-imidazolecarboxylic acid methyl ester in 150 ml of methylene chloride and the mixture is stirred at room temperature for 2 hours. The precipitate is separated off and the filtrate is washed twice using 50 ml of sodium hydrogen carbonate solution (5%) each time, dried over magnesium sulfate and concentrated by evaporation. Chromatography of the residue on silica gel [eluant: ether/hexane (3:1)] yields 1.7 g of a mixture of 1,4-cis-1-(3,4-epoxy-2,2-dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester and 1,4-trans-1-(3,4-epoxy-2,2-dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester in a ratio of 1:1 (m.p. 60°-68° C.).

Workup

  1. customThe precipitate is separated off
  2. washthe filtrate is washed twice
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5e507337aa7e401baaa5ed6e9b7dedc9
Source dataset
uspto-grants-1990_02
Patent number
US04898607

Reaction notes

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