m-Chloroperbenzoic acid → HCID 11978834, compound

HRID 1851605Notes

Reaction equation

HRID 1851605 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]=[CH:21][N:22]=1)=[CH:14]2.ClC1C=CC=C(C(OO)=[O:31])C=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:19][CH:20]=[CH:21][N:22]=1)=[CH:14]2)=[O:31]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 11978835HCID 11978835, compound

Product 1

HCID 11978834HCID 11978834, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-{[(1-methyl-1H-imidazol-2-yl)thio]methyl}-2-(1,3-thiazol-2-yl)-1H-indole (0.087 g) in ethyl acetate was added m-chloroperbenzoic acid (0.070 g) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0) to give the title compound (0.028 g, yield 31%) as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0)

Sources & evidence

ORD record
ord-d3f0b3d3d1c24ab6b8ea847ff91fbfce
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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