Hydrogen Peroxide → 5-(3-dimethylaminopropyl)-5-hydroxy-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

HRID 1284250Notes

Reaction equation

HRID 1284250 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][CH2:5][C:6]1([OH:23])[C:12]2[CH:13]=[C:14]([S:17][CH3:18])[CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2.OO.S(=O)=[O:28].[OH-:30].[Na+]>C(O)(=O)C>[CH3:24][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1([OH:23])[C:12]2[CH:13]=[C:14]([S:17]([CH3:18])(=[O:28])=[O:30])[CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]1=2

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1119Sulfur DioxideHCID 14798Sodium HydroxideHCID 537744045-(3-Dimethylaminopropyl)-5-hydroxy-3-methylmercapto-5H-dibenzo-[a,d]cycloheptene

Product 1

HCID 214120875-(3-dimethylaminopropyl)-5-hydroxy-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(3-Dimethylaminopropyl)-5-hydroxy-3-methylmercapto-5H-dibenzo[a,d]cycloheptene, 21.53 g. (0.063 mole), is dissolved in glacial acetic acid, 250 ml., and the solution is cooled in an ice-bath while 30% hydrogen peroxide, 25.8 ml., is added dropwise with stirring. After standing at room temperature for twenty-two hours, the solution is saturated with sulfur dioxide for 1 hour with periodic cooling in an ice-bath. The solution is made basic with 10 N. sodium hydroxide solution, 625 ml., and extracted with three 300 ml. portions of benzene. After washing the combined extracts with water, solvent is distilled under reduced pressure leaving a yellow oily residue, weight 23.20 g. The oil solidifies on standing at room temperature. Four recrystallizations from methanol-water gives 13.22 g. (57%) of product melting at 170.5°-171.5°C.

Workup

  1. addition, is added dropwise
  2. waitAfter standing at room temperature for twenty-two hours
  3. temperaturewith periodic cooling in an ice-bath
  4. extraction, and extracted with three 300 ml
  5. washAfter washing the combined extracts with water, solvent
  6. distillationis distilled under reduced pressure
  7. customleaving a yellow oily residue, weight 23.20 g
  8. customon standing at room temperature
  9. customFour recrystallizations from methanol-water
  10. customgives 13.22 g

Sources & evidence

ORD record
ord-205431ea5bea4e3388bac2371f631c48
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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