Water → HCID 11978718, compound

HRID 1851607Notes

Reaction equation

HRID 1851607 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7][CH:8]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[CH:15]2)[CH3:9].C(=O)([O-])[OH:25].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].[OH2:36]>C(#N)C>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[S:7]([CH:8]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[CH:15]2)[CH3:9])(=[O:25])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 11978719HCID 11978719, compound

Product 1

HCID 11978718HCID 11978718, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixed solution of 7-{1-[(1-methyl-1H-imidazol-2-yl)thio]ethyl}-2-(1,3-thiazol-2-yl)-1H-indole (0.089 g) in acetonitrile (5 mL) and water (5 mL) was added sodium carbonate-1.5 hydrogen peroxide complex (0.530 g), and the mixture was stirred at room temperature for 4 hr. Saturated aqueous sodium hydrogencarbonate solution and 1N aqueous sodium thiosulfate solution were added, 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 (0.077 g, yield 64%) as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-c1ddb615847f4bca9d4b6c7fd0db1446
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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