Hydrogen Peroxide → HCID 13280947, compound

HRID 1903634Notes

Reaction equation

HRID 1903634 reaction equation
OO.S(=O)(=O)(O)O.[Cl:8][C:9]1[CH:34]=[CH:33][C:12]2[C:13]3[C:14](=[CH:25][N:26]([CH2:29][C:30]([NH2:32])=[O:31])[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-:36].[Na+]>C(O)(=O)C>[Cl:8][C:9]1[CH:34]=[CH:33][C:12]2[C:13]3[CH:27]([CH3:28])[N:26]([CH2:29][C:30]([NH2:32])=[O:31])[C:25](=[O:36])[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 13280939HCID 13280939, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13280947HCID 13280947, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In one portion, 0.7 ml (6.2 mmol) of 30% hydrogen peroxide was added to a 1% solution of concentrated sulfuric acid in acetic acid. After stirring for 1 hour, 1.7 g (4.2 mmol) of 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetamide were added, and the resulting solution was stirred for 30 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 residue was crystallized from ethyl acetate to give 8-chloro-6-(2-chlorophenyl)-1,4-dihydro-1-methyl-3-oxo-2H-pyrrolo[3,4-d][2]benzazepine-2-acetamide as colorless prisms, mp 221°-222° C.

Workup

  1. stirringthe resulting solution was stirred for 30 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 residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-0699364c74124dd38a05a959848939f4
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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