Hydrogen Peroxide → 3-(3-Thienylcarbonyl)benzamide

HRID 2115204Notes

Reaction equation

HRID 2115204 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[O:7])=[CH:2]1.OO.C([O-])(O)=[O:19].[Na+].C(OCC)(=O)C>[NH4+].[OH-].CO>[S:1]1[CH:5]=[CH:4][C:3]([C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]([NH2:12])=[O:19])=[O:7])=[CH:2]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 247233883-(Thiophene-3-carbonyl)benzonitrile

Product 1

HCID 598131583-(3-Thienylcarbonyl)benzamideYield 77.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 14923Ammonium HydroxideSolvent

Procedure

To 1.0 g (4.69 mmol) of 3-(thiophene-3-carbonyl)-benzonitrile in 8 mL of a concentrated NH4OH at room temperature was added 6 mL of 30% H2O2 drop-wise. The white reaction mixture was allowed to stir overnight at room temperature. Next day, to the reaction crude was added 60 mL of a saturated solution of NaHCO3 and 60 mL of ethyl acetate. After removing the aqueous layer, the organic layer was washed with brine, dried over Na2SO4, and concentrated. The concentrated crude was purified by flashy chromatography (dichloromethane:methanol, from 2 to 6% methanol over 16 column volume, then from 6 to 10% methanol over 5 column volume) to obtain 840 mg (77.8% yield) of white solids; 1H NMR 500 MHz (CDCl3) δ 8.27 (m, 2H), 8.15 (m, 2H), 7.93 (m, 1H), 7.74 (m, 1H), 7.65 (t, 1H), 7.55 (m, 2H).

Workup

  1. customNext day, to the reaction crude
  2. customAfter removing the aqueous layer
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. concentrationThe concentrated crude
  7. customwas purified by flashy chromatography (dichloromethane

Sources & evidence

ORD record
ord-6b9b81785d6f4d90988c601d89db07b2
Source dataset
uspto-grants-2008_10
Patent number
US07435822B2

Reaction notes

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