m-Chloroperbenzoic acid → 1-(2,2-Dimethyl-4-oxotetralin-1-yl)-5-imidazolecarboxylic acid methyl ester

HRID 359257Notes

Reaction equation

HRID 359257 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[CH2:23][C:22]2([CH3:32])[CH3:31])[CH:19]=[N:18][CH:17]=1)=[O:15].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[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)[C:8](=[O:10])[CH2:23][C:22]2([CH3:32])[CH3:31])[CH:19]=[N:18][CH:17]=1)=[O:15]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 200684021-(2,2-Dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester

Product 1

HCID 249960101-(2,2-Dimethyl-4-oxotetralin-1-yl)-5-imidazolecarboxylic acid methyl esterYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

10.6 g of 3-chloroperbenzoic acid are added to a solution, cooled to 0° C., of 7.1 g of 1-(2,2-dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester in 200 ml of methylene chloride. The mixture is stirred at room temperature for a further 72 hours. A solution of 7.5 g of sodium hydrogen carbonate in 100 ml of water is then added. The organic phase is separated off, washed with water, dried and concentrated by evaporation. The residue is purified by column chromatography on silica gel using chloroform as eluant. The product-containing fraction is again chromatographed on silica gel using a chloroform/methanol mixture (99.5:0.5). 0.3 g of 1-(2,2-dimethyl-4-oxotetralin-1-yl)-5-imidazolecarboxylic acid methyl ester is obtained in the form of a solid.

Workup

  1. customThe organic phase is separated off
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe residue is purified by column chromatography on silica gel
  6. customThe product-containing fraction is again chromatographed on silica gel using a chloroform/methanol mixture (99.5:0.5)

Sources & evidence

ORD record
ord-66b728e481164a0ea08137d0820aa3bc
Source dataset
uspto-grants-1991_03
Patent number
US05000777

Reaction notes

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