Hydrogen Peroxide → HCID 19735144, compound

HRID 326584Notes

Reaction equation

HRID 326584 reaction equation
[OH-:1].[Na+].OO.[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH3:17])([CH3:16])[N:13]=[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:11]=2[CH:24]=1)#[N:6]>O1CCCC1>[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH3:17])([CH3:16])[N:13]=[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:11]=2[CH:24]=1)(=[O:1])[NH2:6]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 10611577HCID 10611577, compound

Product 1

HCID 19735144HCID 19735144, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 2N sodium hydroxide solution (6 ml) and 30% hydrogen peroxide solution (8 ml) were added dropwise over 20 minutes to a solution of 6-cyano-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.40 g) in tetrahydrofuran(16 ml). The mixture was stirred at room temperature for 40 minutes. The reaction mixture was extracted by addition of ethyl acetate. The organic layer was successively washed with an aqueous sodium bicarbonate solution, an aqueous sodium bisulfite and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was washed with diethyl ether to obtain 6-carbamoyl-2,2-dimethyl-4-(2-pyridyl)-2H-1,3-benzoxazine (0.30 g) (compound 9).

Workup

  1. extractionThe reaction mixture was extracted by addition of ethyl acetate
  2. washThe organic layer was successively washed with an aqueous sodium bicarbonate solution
  3. dry with materialan aqueous sodium bisulfite and saturated saline and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-bb05da78fddc4340a6963da87234d8fd
Source dataset
uspto-grants-1993_12
Patent number
US05270308

Reaction notes

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