Hydrogen Peroxide → HCID 58677395, compound

HRID 747545Notes

Reaction equation

HRID 747545 reaction equation
[CH:1]([C:3]1[S:7][C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=[O:18].[K+].[K+].OO>CS(C)=O>[CH:1]([C:3]1[S:7][C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]([NH2:14])=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 58677388HCID 58677388, compound

Product 1

HCID 58677395HCID 58677395, compoundYield 152.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

Combine 4-(5-formyl-thiophen-2-yloxy)-benzonitrile (772 mg, 3.36 mmol), K2CO3 (powder, 232 mg, 50 mol %) and DMSO (33 mL). Cool down to 0° C. Add hydrogen peroxide (1.01 mL) dropwise. Stir the resulting reaction mixture for 3 hours. Pour the reaction mixture onto H2O (5 mL). Stir for 5 min till a white precipitate appears, then filter and dry under vacuum to provide 633 mg (76%) of the title compound. Part C would be the reaction of this intermediate with an amine to make the final compound. Example 1 was prepared using Method A; Example 2 used Medthod B.

Workup

  1. customthe resulting reaction mixture for 3 hours
  2. additionPour the reaction mixture onto H2O (5 mL)
  3. stirringStir for 5 min till a white precipitate
  4. filtrationfilter
  5. customdry under vacuum

Sources & evidence

ORD record
ord-12a42b0c120148658cc97cd21e3de44b
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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