Hydrogen Peroxide → HCID 15959494, compound

HRID 1708222Notes

Reaction equation

HRID 1708222 reaction equation
[Se](=O)=O.[CH2:4]([NH:6][C:7]([C:9]1[S:13][C:12]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:11]=2[C:10]=1[O:20][CH:21]([CH3:23])[CH3:22])=[O:8])[CH3:5].OO.C([O-])(O)=[O:27].[Na+]>CO.CCOC(C)=O>[CH2:4]([NH:6][C:7]([C:9]1[S:13](=[O:27])[C:12]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:11]=2[C:10]=1[O:20][CH:21]([CH3:22])[CH3:23])=[O:8])[CH3:5]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24007Selenium DioxideHCID 516892Sodium BicarbonateHCID 10017280HCID 10017280, compound

Product 1

HCID 15959494HCID 15959494, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Selenium dioxide is added to a room temperature solution of N-ethyl-5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxamide (195 mg, 0.66 mmol) in 8 mL of MeOH containing 530 μL of hydrogen peroxide (30% aqueous). The reaction mixture is stirred overnight at room temperature. The reaction mixture is poured into EtOAc and saturated NaHCO3. The organic phase is washed with saturated NaHCO3, 1N HCl, then brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid is chromatographed, eluting with a gradient of 1:9 EtOAc:CH2Cl2 to 1:1 EtOAc:CH2Cl2, to provide 96 mg (47%) of N-ethyl-5-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxamide -1-oxide; mp 88°-90° C.

Workup

  1. washThe organic phase is washed with saturated NaHCO3, 1N HCl
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid is chromatographed
  6. washeluting with a gradient of 1:9 EtOAc

Sources & evidence

ORD record
ord-87a5f5ded950497eb2b3401dd5c6a994
Source dataset
uspto-grants-1994_10
Patent number
US05356926

Reaction notes

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