Hydrogen Peroxide → HCID 178494303, compound

HRID 1487981Notes

Reaction equation

HRID 1487981 reaction equation
[CH:1]1([C:5]2[C:12]([C:13]3[NH:17][C:16]([O:18][CH3:19])=[N:15][N:14]=3)=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH3:20])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[NH4+].[OH-:22].OO>CCO>[CH:1]1([C:5]2[C:12]([C:13]3[NH:17][C:16]([O:18][CH3:19])=[N:15][N:14]=3)=[CH:11][C:8]([C:9]([NH2:10])=[O:22])=[C:7]([CH3:20])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 178494302HCID 178494302, compound2×

Product 1

HCID 178494303HCID 178494303, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-cyclobutyl-5-(5-methoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzonitrile (compound 89.7, 0.15 g, 0.53 mmol) in EtOH (10 mL) was added NH4OH (0.18 mL, 2.66 mmol, 14.8 M in H2O), followed by H2O2 (1.8 mL, 26.6 mmol, 50% in H2O). The mixture was stirred at room temperature overnight, then cooled to 0° C. and carefully quenched with 1 M Na2S2O3 solution (26 mL). The mixture was extracted with EtOAc (×2) and the combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC (5% MeOH in CH2Cl2) to yield 0.1 g (63%) of the title compound as a white solid. m/z (ES+) 287(M+H)+. 1H NMR (400 MHz, Methanol-d4) δ7.50 (s, 1H), 7.33 (s, 1H), 4.03 (s, 3H), 3.95-4.05 (m, 1H), 2.51 (s, 3H), 2.23-2.11 (m, 2H), 2.11-1.88 (m, 3H), 1.83-1.71 (m, 1H).

Workup

  1. temperaturecooled to 0° C.
  2. customcarefully quenched with 1 M Na2S2O3 solution (26 mL)
  3. extractionThe mixture was extracted with EtOAc (×2)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by prep-TLC (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-84d84824e62c4c758c4f948dd576e1a8
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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