Hydrogen Peroxide → HCID 178513638, compound

HRID 1023870Notes

Reaction equation

HRID 1023870 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2[O:8][CH2:9][CH:10]=[C:11]2[CH2:16][CH2:15][CH:14]([C:17]#[N:18])[CH2:13][CH2:12]2)[N:3]=[CH:2]1.C([O-])([O-])=[O:24].[K+].[K+].OO>CS(C)=O>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2[O:8][CH2:9][CH:10]=[C:11]2[CH2:12][CH2:13][CH:14]([C:17]([NH2:18])=[O:24])[CH2:15][CH2:16]2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 178509780HCID 178509780, compound

Product 1

HCID 178513638HCID 178513638, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(2-(2-(1H-imidazol-4-yl)phenoxy)ethylidene)cyclohexanecarbonitrile (90 mg, 0.307 mmol) in DMSO (3 mL) at room temperature was added K2CO3 (42 mg, 0.307 mmol) followed by H2O2 (30%, 0.7 mL, 6.14 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) to yield the desired amide as a white solid (40 mg, 0.129 mmol, 42%). 1H NMR (DMSO-d6): 1.41-1.51 (m, 4H), 1.71-1.82 (m, 4H), 2.17-2.20 (m, 1H), 4.05-4.11 (m, 2H), 6.66 (d, 1H, J=10.5 Hz), 6.93 (t, 1H, J=7.5 Hz), 7.02 (d, 1H, J=8.1 Hz), 7.11 (d, 1H, J=7.2 Hz), 7.15 (s, 2H), 7.51 (s, 1H), 7.68 (s, 1H), 8.08 (d, 1H, J=7.5 Hz), 12.05 (br s, 1H).

Workup

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

Sources & evidence

ORD record
ord-ceb43b35c22642088d8c142eab820599
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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