1-Methylimidazole → HCID 59134367, compound

HRID 2425345Notes

Reaction equation

HRID 2425345 reaction equation
[CH3:1][C:2]1([CH3:18])[O:17][C:6]2=[CH:7][C:8]3[C:9]([CH3:16])=[CH:10][C:11]([CH3:15])=[N:12][C:13]=3[CH:14]=[C:5]2[CH:4]=[CH:3]1.CN1C=CN=C1.Cl[O-].[Na+].S([O-])([O-])(=[O:30])=S.[Na+].[Na+]>C(OCC)(=O)C.O>[O:30]1[C@@H:4]2[C:5]3[C:6]([O:17][C:2]([CH3:18])([CH3:1])[C@H:3]12)=[CH:7][C:8]1[C:9]([CH3:16])=[CH:10][C:11]([CH3:15])=[N:12][C:13]=1[CH:14]=3

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 24477Sodium ThiosulfateHCID 23665760Sodium Hypochlorite2×HCID 59134423HCID 59134423, compound

Product 1

HCID 59134367HCID 59134367, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline (4.64 g, 19.4 mmol) in ethyl acetate (70 mL), N-methyl imidazole (0.303 mL, 3.88 mmol) and Ph,Ph salen manganese complex (201 mg, 0.194 mmol) were added at room temperature and sodium hypochlorite aqueous solution (25.6 g, 1.513 mol/kg, 38.8 mmol) was added dropwise in water bath, and the resulting mixture was stirred in water bath for 1 hour. Further, in water bath, sodium hypochlorite aqueous solution (25.6 g, 1.513 mol/kg, 38.8 mmol) was added, and the resulting mixture was stirred in water bath for 1 hour. Upon the completion of the reaction, sodium thiosulfate aqueous solution was added to the reaction solution, the resulting mixture was filtered through celite and extracted. The organic phase was washed with sodium hydrogencarbonate aqueous solution and then with sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=1/3) and the aimed product was obtained (yield: 68%).

Workup

  1. additionwas added to the reaction solution
  2. filtrationthe resulting mixture was filtered through celite
  3. extractionextracted
  4. washThe organic phase was washed with sodium hydrogencarbonate aqueous solution
  5. dry with materialwith sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by column chromatography (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-e82d623893a84c829add0ad992504753
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

Loading…