HCID 23464801, compound → HCID 23464790, compound

HRID 444234Notes

Reaction equation

HRID 444234 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][C:7]3[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=3[CH:9]([CH3:13])[C:10]([CH3:12])(O)[C:4]=2[CH:3]=1>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][C:7]3[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=3[C:9]([CH3:13])=[C:10]([CH3:12])[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 23464801HCID 23464801, compound

Product 1

HCID 23464790HCID 23464790, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A suspension of 7.7 g of 2-bromo-10,11-dimethyl-11-hydroxy-10,11-dihydro-dibenz[b,f]thiepine in 40 ml of 20% sulfuric acid is refluxed for 36 hours, with rapid stirring. The mixture is then cooled and extracted with three times 50 ml of ether. The ether extracts are combined, washed with water until neutral, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue is dissolved in 32 ml of 20% ethanolic potassium hydroxide solution and the solution is refluxed for 40 hours. It is then concentrated to dryness under reduced pressure and the residue is extracted with 100 ml of ether. The ether solution is washed with 20 ml of water, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue is dissolved in 300 ml of methanol, a small amount of insoluble matter is filtered off and the filtrate is concentrated under reduced pressure. 2-Bromo-10,11-dimethyl-dibenz[b,f]thiepine is obtained in the form of yellowish crystals; melting point 108°-111°.

Workup

  1. temperatureis refluxed for 36 hours, with rapid stirring
  2. temperatureThe mixture is then cooled
  3. extractionextracted with three times 50 ml of ether
  4. washwashed with water until neutral,
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. dissolutionThe residue is dissolved in 32 ml of 20% ethanolic potassium hydroxide solution
  8. temperaturethe solution is refluxed for 40 hours
  9. concentrationIt is then concentrated to dryness under reduced pressure
  10. extractionthe residue is extracted with 100 ml of ether
  11. washThe ether solution is washed with 20 ml of water
  12. dry with materialdried over magnesium sulfate
  13. customevaporated to dryness under reduced pressure
  14. dissolutionThe residue is dissolved in 300 ml of methanol
  15. filtrationa small amount of insoluble matter is filtered off
  16. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-74172d2600f042aab312b6c4a8ff72f7
Source dataset
uspto-grants-1981_04
Patent number
US04263315

Reaction notes

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