Hydrogen Peroxide → HCID 178513624, compound

HRID 1023869Notes

Reaction equation

HRID 1023869 reaction equation
[NH:1]1[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]#[N:9])=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=[O:15].[K+].[K+].OO>CS(C)=O>[NH:3]1[CH:4]=[C:5]([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]([NH2:9])=[O:15])[N:1]=[CH:2]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 13552870HCID 13552870, compound

Product 1

HCID 178513624HCID 178513624, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(1H-imidazol-5-yl)benzonitrile (85 mg, 0.502 mmol) in DMSO (3 mL) at room temperature was added K2CO3 (69 mg, 0.502 mmol) followed by H2O2 (30%, 1.1 mL, 10.04 mmol). After stirring for 16 h, the reaction was concentrated and the crude product was purified by flash column chromatography (silica gel, 10% MeOH/DCM followed by 10% MeOH/EtOAc) to yield the desired amide as a white solid (70 mg, 0.374 mmol, 75%). 1H NMR (DMSO-d6): 7.20-7.35 (m, 5H), 7.66 (s, 1H), 7.75 (s, 1H), 7.83 (s, 1H), 12.01 (br s, 1H).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe crude product was purified by flash column chromatography (silica gel, 10% MeOH/DCM followed by 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-9d66ca79b74f405da16f23516d218be2
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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