Hydrogen Peroxide → HCID 13280945, compound

HRID 1903631Notes

Reaction equation

HRID 1903631 reaction equation
OO.S(=O)(=O)(O)O.[Cl:8][C:9]1[CH:31]=[CH:30][C:12]2[C:13]3[C:14](=[CH:25][N:26]([CH3:29])[C:27]=3[CH3:28])[CH2:15][N:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:11]=2[CH:10]=1.S(=O)(O)[O-:33].[Na+]>C(O)(=O)C>[Cl:8][C:9]1[CH:31]=[CH:30][C:12]2[C:13]3[CH:27]([CH3:28])[N:26]([CH3:29])[C:25](=[O:33])[C:14]=3[CH2:15][N:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 13280935HCID 13280935, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13280945HCID 13280945, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In one portion, 0.7 ml (5.9 mmol) of a 30% hydrogen peroxide solution was added to 33 ml of a 1% solution of concentrated sulfuric acid in acetic acid. After stirring for 1 hour, 1.8 g (5.0 mmol) of 8-chloro-6-(2-chlorophenyl)-1,2-dimethyl-2H,4H-pyrrolo[3,4-d][2]benzazepine were added, and the resulting solution was stirred for 20 minutes. The excess peracid was discharged by the addition of saturated aqueous sodium bisulfite solution, and the mixture was concentrated at reduced pressure. The residue was partitioned between methylene chloride and water and basififed with concentrated ammonium hydroxide solution. The methylene chloride solution was washed with brine, dried over anhydrous sodium sulfate and concentrated at reduced pressure to a yellow residue. Crystallization from ethyl aceatate gave 8-chloro-6-(2-chlorophenyl)-1,4-dihydro-1,2-dimethylpyrrolo[3,4-d][2]benzazepin-3(2H)-one as pale yellow prisms, mp 207°-208° C.

Workup

  1. stirringthe resulting solution was stirred for 20 minutes
  2. concentrationthe mixture was concentrated at reduced pressure
  3. customThe residue was partitioned between methylene chloride and water and basififed with concentrated ammonium hydroxide solution
  4. washThe methylene chloride solution was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure to a yellow residue
  7. customCrystallization from ethyl aceatate

Sources & evidence

ORD record
ord-c4460e0a50f84967862d9fd13aee9c2b
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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