1-Methylimidazole → HCID 59134367, compound

HRID 1993465Notes

Reaction equation

HRID 1993465 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 962WaterSolvent2×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 (XX) (201 mg, 0.194 mmol) were added at room temperature and aqueous sodium hypochlorite solution (25.6 g, 1.513 mol/kg, 38.8 mmol) was added dropwise, and the resulting mixture was stirred for 1 hour. Further, in water bath, aqueous sodium hypochlorite 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, aqueous sodium thiosulfate solution was added to the reaction solution, the resulting mixture was filtered through celite and extracted. The organic phase was washed with aqueous sodium hydrogencarbonate solution and then with aqueous sodium chloride 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 aqueous sodium hydrogencarbonate solution
  5. dry with materialwith aqueous sodium chloride 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-dacc77eba3a94ec183652fae7cbb350c
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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