Acetic Acid → HCID 9890141, compound

HRID 1637201Notes

Reaction equation

HRID 1637201 reaction equation
OO.[OH2:3].[C:4]1([S:10][C:11]2[C:12]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:21][C:13]=3[S:14][C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=[O:35])C>>[C:4]1([S:10]([C:11]2[C:12]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:21][C:13]=3[S:14][C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:35])=[O:3])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 9931973HCID 9931973, compound

Product 1

HCID 9890141HCID 9890141, compound

Conditions

Temperature
100 °C

Procedure

Hydrogen peroxide in water (0.42 ml of 30% w/v, 3.75 mmol) was added to a solution of ethyl 3-(phenylsulfanyl)-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Example 1, 633 mg, 1.5 mmol) in acetic acid (4.5 ml). The mixture was heated to 100° C. for 90 minutes. The solvents were removed by evaporation under reduced pressure, and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was separated, dried (magnesium sulfate) and concentrated under vacuo, and the residue flash chromatographed on silica gel using 1% methanol in dichloromethane as eluant. The less polar product was isolated and crystallised from dichloromethane and diethyl ether to give the title compound as a colourless solid (230 mg).

Workup

  1. customThe solvents were removed by evaporation under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under vacuo
  6. customthe residue flash chromatographed on silica gel using 1% methanol in dichloromethane as eluant
  7. customThe less polar product was isolated
  8. customcrystallised from dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-d084c8ecde014ad2a7f8a5439727b9e4
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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