Dimethyl Sulfoxide → HCID 28825277, compound

HRID 228192Notes

Reaction equation

HRID 228192 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=[O:2].CS(C)=[O:20].C(=O)([O-])[O-].[K+].[K+].OO>O>[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]([NH2:13])=[O:20])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 6138064-(4-Formylphenoxy)benzonitrile

Product 1

HCID 28825277HCID 28825277, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 4-(4-Formyl-phenoxy)-benzonitrile (3.6 g, 16.1 mmol), dimethylsulfoxide (25 mL), potassium carbonate (2.1 g, 15.2 mmol), and 3 mL of 30% hydrogen peroxide solution. Stir 18 h at ambient temperature. Dilute with 100 mL of water, extract with ethyl acetate (3×100 mL). Wash the organic phase with 100 mL of water, and 50 mL of brine. Dry the organic phase over sodium sulfate, filter, and concentrate under vacuum. Purify via a Biotage Flash 40L system using 75:25 hexanes/ethyl acetate as eluting solvent to give 3.0 g (77%) of the title compound: 1H NMR (chloroform-d): 9.95 (s, 1H), 7.88 (m, 4H), 7.12 (m, 4H), 5.29-5.14 (br m, 2H).

Workup

  1. extractionextract with ethyl acetate (3×100 mL)
  2. washWash the organic phase with 100 mL of water, and 50 mL of brine
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify via a Biotage Flash 40L system
  7. washas eluting solvent

Sources & evidence

ORD record
ord-b17a6087ee2245a89c9249cca344215d
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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