Hydrogen Peroxide → HCID 13280944, compound

HRID 1903629Notes

Reaction equation

HRID 1903629 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][NH:26][C:27]=3[CH2:28][CH3:29])[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]([CH2:28][CH3:29])[NH:26][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 132809348-chloro-6-(2-chlorophenyl)-1-ethyl-2H,4H-pyrrolo[3,4-d][2]benzazepineHCID 23665763Sodium Bisulfite

Product 1

HCID 13280944HCID 13280944, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In one portion, 0.9 ml (7.9 mmol) of 30% hydrogen peroxide was added to 40 ml of a 1% solution of concentrated sulfuric acid in acetic acid. After stirring for 1 hour, 2.0 g (5.6 mmol) of 8-chloro-6-(2-chlorophenyl)-1-ethyl-2H,4H-pyrrolo[3,4-d][2]benzazepine were added, and the resulting mixture 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 neutralized with concentrated ammonium hydroxide solution. The methylene chloride solution was washed with brine, dried over anhydrous sodium sulfate, and concentrated at reduced pressure. The resulting oil was crystallized from ether to give 8-chloro-6-(2-chlorophenyl)-1-ethyl-1,4-dihydropyrrolo[3,4-d][2]benzazepin-3(2H)-one as yellow prisms, mp 233°-235° C. Recrystallization from a mixture of ethyl acetate and methanol gave colorless prims, mp 236°-237° C.

Workup

  1. stirringthe resulting mixture was stirred for 20 minutes
  2. concentrationthe mixture was concentrated at reduced pressure
  3. customThe residue was partitioned between methylene chloride and water and neutralized 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
  7. customThe resulting oil was crystallized from ether

Sources & evidence

ORD record
ord-a18503db013a497eb9fd3778341c3b5f
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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