Hydrogen Peroxide → HCID 44554074, compound

HRID 1254052Notes

Reaction equation

HRID 1254052 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.OO.C([O-])([O-])=[O:32].[K+].[K+]>CS(C)=O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:22]=[CH:23][C:24]([C:25]([NH2:26])=[O:32])=[CH:27][CH:28]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 44553222HCID 44553222, compound

Product 1

HCID 44554074HCID 44554074, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-2-phenyl-1H-imidazol-4-yl}benzonitrile (Example 2, 25 mg, 0.062 mmol) in 2 mL DMSO at 0° C. was added lint of 30% H2O2 (aq). A catalytic amount of K2CO3 was added and the reaction was stirred at 50° C. for 60 min. The reaction mixture was diluted with MeOH and the product was purified by reverse phase HPLC. The fractions containing the product were collected and diluted with EtOAc, washed with aq NaHCO3, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford the title compound. 1H NMR (500 MHz, (CDCl3): 8.23 (d, 2H), 7.84 (d, 2H), 7.78 (m, 2H), 7.58 (m, 3H), 7.28 (d, 2H), 7.08 (d, 2H), 6.23 (broad s, 1H), 5.82 (broad s, 1H), 3.72 (s, 3H). LCMS: m/z 420 (M+H)+.

Workup

  1. customthe product was purified by reverse phase HPLC
  2. additionThe fractions containing the product
  3. customwere collected
  4. additiondiluted with EtOAc
  5. washwashed with aq NaHCO3, water, and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f2aa9ba5e0f54f3f9e7feb09a167ed6a
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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