Hydrogen Peroxide → HCID 10298064, compound

HRID 1297131Notes

Reaction equation

HRID 1297131 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:6][CH:5]([CH2:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]#[N:29])[C:4]1=[O:33])[CH3:2].[OH:34]O.[OH-].[Na+]>C(O)C.O>[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:6][CH:5]([CH2:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[C:28]([NH2:29])=[O:34])[C:4]1=[O:33])[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 69461612HCID 69461612, compound

Product 1

HCID 10298064HCID 10298064, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 40 mg (0.91 mmol) of 3-[(1-ethyl-7,8-dimethoxy-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)methyl]benzonitrile (IIcp) in 1 ml of ethanol, add under an inert atmosphere 27 μl (0.27 mmol) of 30% (m/m) H2O2 in water, 36 μl (0.018 mmol) of 0.5 M NaOH in water. Stir under reflux for 12 hours. Evaporate to dryness. Take up in a 25 ml of a water-ice mixture. Filter the solid, wash twice with 20 ml of water and once with 5 ml of ether. One obtains 24 mg of the abovenamed product as a white powder. Yield: 59%. M: 111–113° C. 1H-NMR (CDCl3, 200 MHz): d 1.10 (s, 3H, CH3), 3.50–3.75 (m, 6H, 1H —CH2Ph+1H —NCH2+CH+OCH3), 3.98–4.11 (m, 4H, 1H —CH2Ph+OCH3), 4.38–4.49 (m, 1H —NCH2), 5.91 (m, 1H exchangeable CO—NH2), 6.26 (m, 1H exchangeable CO—NH2), 6.66 (s, 1H Ar), 6.85 (s, 1H Ar), 7.30–7.86 (m, 9H Ar).

Workup

  1. temperatureunder reflux for 12 hours
  2. customEvaporate to dryness
  3. filtrationFilter the solid
  4. washwash twice with 20 ml of water and once with 5 ml of ether

Sources & evidence

ORD record
ord-157d57087e6140fdb1452b1bb0074845
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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