Hydrogen Peroxide → HCID 57652741, compound

HRID 424834Notes

Reaction equation

HRID 424834 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[C:12]([CH:30]([CH3:32])[CH3:31])[N:11]=[N:10]1.C(=O)([O-])[O-:34].[K+].[K+].OO>CS(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([NH2:29])=[O:34])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[C:12]([CH:30]([CH3:32])[CH3:31])[N:11]=[N:10]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66704085HCID 66704085, compound

Product 1

HCID 57652741HCID 57652741, compoundYield 64,171.699%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 4′-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-biphenyl-4-carbonitrile (0.150 mg) in dimethyl sulfoxide (1.2 mL) is added potassium carbonate (0.03 g) and 50% aqueous hydrogen peroxide (0.2 mL). The reaction mixture is allowed to stir at room temperature for 30 minutes. The reaction mixture is diluted with water (55 mL), cooled to 0° C., and filtered. The resulting solids are washed with cold (−78° C.) hexanes. The white solids are allowed to dry under reduced pressure to give the title compound (0.100 g, 64%). 1H NMR (300 MHz, CDCl3) δ 7.9 (d, 2H), 7.6 (d, 2H), 7.5 (m, 5H), 6.9 (d, 2H), 5.0 (s, 2H), 3.3 (p, 1H), 1.5 (d, 6H);′ APCI/MS m/e 481 (M+1), HPLC purity 98.5%.

Workup

  1. temperaturecooled to 0° C.
  2. filtrationfiltered
  3. washThe resulting solids are washed with cold (−78° C.) hexanes
  4. customto dry under reduced pressure

Sources & evidence

ORD record
ord-5939bfe068ad43549e115bc0085454bd
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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