Hydrogen Peroxide → HCID 178467490, compound

HRID 541361Notes

Reaction equation

HRID 541361 reaction equation
[CH:1]1([C:5]2[C:12]([C:13]3[NH:17][C:16]([O:18][CH2:19][CH3:20])=[N:15][N:14]=3)=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH3:21])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[NH4+].[OH-:23].OO>CCO>[CH:1]1([C:5]2[C:12]([C:13]3[NH:17][C:16]([O:18][CH2:19][CH3:20])=[N:15][N:14]=3)=[CH:11][C:8]([C:9]([NH2:10])=[O:23])=[C:7]([CH3:21])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 1784674894-Cyclobutyl-5-(5-ethoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzonitrile

Product 1

HCID 178467490HCID 178467490, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-cyclobutyl-5-(5-ethoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzonitrile (219.7, 0.15 g, 0.53 mmol) in EtOH (10 ml) was added NH4OH (0.18 ml, 2.66 mmol, 14.8 N in H2O) followed by H2O2 (1.8 ml, 26.6 mmol, 50% in H2O). The mixture was stirred at room temperature overnight. The mixture was cooled to 0° C. and quenched carefully with 1N Na2S2O3 solution (26 ml). The mixture was extracted with EtOAc (×2) and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified with prep-TLC (5% MeOH in CH2Cl2). Yield: 0.1 g, white solid, 62.5%. m/z (ES−) 299 (M−H)−.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched carefully with 1N Na2S2O3 solution (26 ml)
  3. extractionThe mixture was extracted with EtOAc (×2)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with prep-TLC (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a3e3d45d5ba840c6862017f32b55cf7a
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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