Hydrogen Peroxide → HCID 178513647, compound

HRID 404252Notes

Reaction equation

HRID 404252 reaction equation
C([N:20]1[CH:24]=[C:23]([C:25]2[CH:40]=[CH:39][CH:38]=[CH:37][C:26]=2[O:27][CH2:28][C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=[O:42].[K+].[K+].OO.[OH-].[Na+]>CN(C=O)C.O.C(O)(=O)C.CO>[NH:20]1[CH:24]=[C:23]([C:25]2[CH:40]=[CH:39][CH:38]=[CH:37][C:26]=2[O:27][CH2:28][C:29]2[CH:36]=[CH:35][C:32]([C:33]([NH2:34])=[O:42])=[CH:31][CH:30]=2)[N:22]=[CH:21]1

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 58294125HCID 58294125, compound

Product 1

HCID 178513647HCID 178513647, compoundYield 120.6%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-((2-(1-trityl-1H-imidazol-4-yl)phenoxy)methyl)benzonitrile (0.328 mmol) in DMF (3 mL) at rt was added K2CO3 (0.164 mmol) followed by H2O2 (1.64 mmol, 30% aq. solution). After stirring for 30 min the reaction mixture was diluted with H2O (10 mL) and the aqueous phase was extracted with EtOAc (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated to afford the crude product. The crude was dissolved in a mixture of glacial acetic acid (1.0 mL) and MeOH (4.0 mL) and was heated to 80° C. for 2h. The solution was allowed to cool to room temperature and the pH was adjusted to ˜10 with 10% NaOH (aq). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water, brine, and dried over Na2SO4. The solvent was removed in vacuo to afford the crude residue, which was purified by flash column chromatography on silica gel to afford the desired product (58 mg, 60% yield). 1H NMR: 5.23 (s, 2H), 5.71 (br s, 1H), 6.24 (br s, 1H), 7.01 (d, 1H, J=8.28 Hz), 7.07 (t, 1H, J=7.44 Hz), 7.21 (m, 2H), 7.48 (s, 1H), 7.53 (d, 1H, J=8.19 Hz), 7.60 (s, 1H), 7.85 (d, 1H, J=8.19 Hz)

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×25 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated
  4. customto afford the crude product
  5. temperatureto cool to room temperature
  6. extractionThe aqueous phase was extracted with EtOAc (3×20 mL)
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed in vacuo
  10. customto afford the crude residue, which
  11. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ac00157f3c6447d8b646672bfb7f714b
Source dataset
uspto-grants-2014_06
Patent number
US08748469B2

Reaction notes

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