Hydrogen Peroxide → HCID 57900523, compound

HRID 1949841Notes

Reaction equation

HRID 1949841 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[NH:11][N:10]=[C:9]1[C:14]1[S:29][C:17]2[C:18]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1.C(=O)([O-])[O-:31].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[NH:11][N:10]=[C:9]1[C:14]1[S:29][C:17]2[C:18]3[CH:26]=[CH:25][C:24]([C:27]([NH2:28])=[O:31])=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 57900228HCID 57900228, compound

Product 1

HCID 57900523HCID 57900523, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(4-(2-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-8-carbonitrile 278 in DMSO was treated with potassium carbonate and the resultant yellow suspension cooled to 0° C. The reaction mixture was treated dropwise with hydrogen peroxide (30% wt. in water). The whole was warmed to room temperature and the reaction quenched with sat. NaHSO3. Extraction with ethylacetate and concentration gave a residue that was purified by reverse phase HPLC to give 295 as a colorless solid.

Workup

  1. temperatureThe whole was warmed to room temperature
  2. customthe reaction quenched with sat. NaHSO3
  3. extractionExtraction
  4. concentrationwith ethylacetate and concentration
  5. customgave a residue that
  6. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-67fde46871ea466ca02e0322aebe2e70
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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