Hydrogen Peroxide → HCID 10043600, compound

HRID 747544Notes

Reaction equation

HRID 747544 reaction equation
[CH2:1]([NH:9][CH2:10][C:11]1[S:15][C:14]([O:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=[O:26].[K+].[K+].OO>CS(C)=O>[CH2:1]([NH:9][CH2:10][C:11]1[S:15][C:14]([O:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([NH2:22])=[O:26])=[CH:23][CH:24]=2)=[CH:13][CH:12]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 58677376HCID 58677376, compound

Product 1

HCID 10043600HCID 10043600, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

Combine 4-[5-(phenethylamino-methyl)-thiophen-2-yloxy]-benzonitrile ((139 mg, 0.415 mmol), K2CO3 (powder, 28 mg, 50 mol %) and DMSO (4 mL). Cool down to 0° C. Add hydrogen peroxide (0.124 mL) dropwise. Stir the resulting reaction mixture for 2.5 h. Partition the reaction mixture between H2O (5 mL) and CH2Cl2 (3×5 mL). Dry over sodium sulfate, filter and concentrate. Purify the residue through an SCX column with ammonia (2.0 M in methanol) to provide 105 mg (75%) of the title compound. Mass spectrum (ion spray): m/z=353.0 (M+1). 1H NMR (Cl3CD): 7.80 (d, J=8.7 Hz, 2H), 7.34-7.22 (m, 5H), 7.12 (d, J=8.7 Hz, 2H), 6.65 (d, J=3.37 Hz, 1H), 6.44 (d, J=3.7 Hz, 1H), 5.96 (bs, 2H), 3.93 (s, 2H), 2.97 (t, J=6.4 Hz, 2H), 2.85 (t, J=6.5 Hz, 2H).

Workup

  1. customthe resulting reaction mixture for 2.5 h
  2. customPartition the reaction mixture between H2O (5 mL) and CH2Cl2 (3×5 mL)
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue through an SCX column with ammonia (2.0 M in methanol)

Sources & evidence

ORD record
ord-d334a11e02864d888310592eb1552af7
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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