Hydrogen Peroxide → HCID 58204932, compound

HRID 1629055Notes

Reaction equation

HRID 1629055 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[C:11]3[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:10]=3[O:9][CH2:8][CH2:7][N:6]2[CH:20]=1)#[N:2].C(=O)([O-])[O-:22].[K+].[K+].O.OO>CS(C)=O>[C:1]([C:3]1[N:4]=[C:5]2[C:11]3[CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[CH:15][C:10]=3[O:9][CH2:8][CH2:7][N:6]2[CH:20]=1)(=[O:22])[NH2:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962Water2×HCID 11430Potassium CarbonateHCID 58205026HCID 58205026, compound

Product 1

HCID 58204932HCID 58204932, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-cyano-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate (220 mg, 0.82 mmol) was dissolved in 4.0 ml of dimethyl sulfoxide and treated with a solution of potassium carbonate (136 mg, 0.980 mmol) in water (1.60 mL, 88.8 mmol). After cooling at 0° C., hydrogen peroxide (0.751 mL, 9.80 mmol) was added slowly. The mixture was stirred at room temperature for 2 hours. The mixture was diluted with20 ml of water and extracted with ethyl acetate (3×20 ml). The oprganic extracts were washed with 5% sodium thiosufate, sat. NaHCO3, brine, dried over sodium sulfate and concentrated to give 180 mg (77%) of crude methyl 2-carbamoyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-10-carboxylate. MS(ESI+): 288.0.

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washThe oprganic extracts were washed with 5% sodium thiosufate, sat. NaHCO3, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16d382d32cfc4e53ace5eda22b3443d0
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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