Hydrogen Peroxide → HCID 3040672, compound

HRID 1579157Notes

Reaction equation

HRID 1579157 reaction equation
OO.Cl.[CH2:4]([S:6][C:7]1[CH:27]=[CH:26][C:10]2[N:11]([CH3:25])[C:12]3[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=3[CH:14]=[C:15]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:9]=2[CH:8]=1)[CH3:5].[OH2:28].[OH-:29].[Na+]>C(O)(=O)C>[CH2:4]([S:6]([C:7]1[CH:27]=[CH:26][C:10]2[N:11]([CH3:25])[C:12]3[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=3[CH:14]=[C:15]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:9]=2[CH:8]=1)(=[O:29])=[O:28])[CH3:5]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 30406695H-Dibenz(b,f)azepine, 10-(2-(dimethylamino)ethyl)-8-(ethylthio)-5-methyl-, hydrochloride

Product 1

HCID 3040672HCID 3040672, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

5.1 ml of 30% hydrogen peroxide were added dropwise in 10 minutes to a solution of 4.25 g of 2-ethylthio-5-methyl-11-(β-dimethylaminoethyl) [5H] dibenzo (b,f) azepine hydrochloride in 42.5 ml of acetic acid heated to 65°C and the mixture was stirred at 65°C for 4 hours and then was cooled. The mixture was poured into 200 ml of ice and water and the solution was made alkaline by addition of sodium hydroxide. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel with a 95-5 mixture of chloroform-methanol as eluant which was distilled to obtain 2.85 g of 2-ethylsulfonyl-5-methyl-11-(β-dimethylaminoethyl) [5H] dibenzo (b,f) azepine.

Workup

  1. temperaturewas cooled
  2. extractionThe mixture was extracted with methylene chloride
  3. washthe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel with a 95-5 mixture of chloroform-methanol as eluant which
  7. distillationwas distilled

Sources & evidence

ORD record
ord-229a4814254d46f6b2d0f91ab8665352
Source dataset
uspto-grants-1976_01
Patent number
US03931151

Reaction notes

Loading…