Methanol → 2-chloro-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 1938241Notes

Reaction equation

HRID 1938241 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=O)[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=O)[C:4]=2[CH:3]=1.[B].CSC.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 134665322-Chloro-5H-dibenzo[b,e]azepine-6,11-dione

Product 1

HCID 537916382-chloro-6,11-dihydro-5H-dibenz[b,e]azepineYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 7.28 g of 2-chloro-5H-dibenz-[b,e]azepine-6,11-dione in 25 ml of anhydrous tetrahydrofuran, under argon, is added dropwise 8.5 ml of (10M) boron-dimethyl sulfide. The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is heated at reflux for 3 hours and cooled to room temperature. While stirring, 25 ml of methyl alcohol is carefully added, followed by 100 ml of 2N NaOH. The reaction mixture is heated at reflux for 24 hours and the solid collected. The solid is dissolved in methylene chloride and washed with 2N citric acid, water and dried (Na2SO4). The volatiles are evaporated in vacuo to give 4.16 g of a residue which is crystallized from ethyl acetate-hexane to give 2.05 g of the desired product as a crystalline solid, m.p. 137°-141° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled to room temperature
  4. stirringWhile stirring
  5. temperatureThe reaction mixture is heated
  6. temperatureat reflux for 24 hours
  7. customthe solid collected
  8. dissolutionThe solid is dissolved in methylene chloride
  9. washwashed with 2N citric acid, water
  10. dry with materialdried (Na2SO4)
  11. customThe volatiles are evaporated in vacuo

Sources & evidence

ORD record
ord-4b76805a14b841bfb30c2dc258247306
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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