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Methanol → 9Chloro-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 1457621
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1457621
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=O)[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=O)[C:6]=2[CH:18]=1.[B].CSC.CO>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][C:6]=2[CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 540117039-Chloro-5H-dibenz[b,e]azepin-6,11-dione

Produkt 1

HCID 541749289Chloro-6,11-dihydro-5H-dibenz[b,e]azepineAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a mixture of 7.28 g 9-chloro-5H-dibenz-[b,e]azepin-6,11-dione in 25 ml of tetrahydrofuran under argon is added 8.5 ml of 10 molar boron-dimethylsulfide in tetrahydrofuran. The mixture is stirred 18 hours at room temperature, 30 ml of tetrahydrofuran added and the mixture refluxed for 3 hours (solids dissolved). The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2N NaOH. The mixture is refluxed overnight and filtered. The solid is extracted with dichloromethane and the extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed to give 4.2 g of solid which is triturated with ethyl acetate-hexane (1:2) to give crystals, m.p. 137° C. to 141° C.

Aufarbeitung

  1. temperaturethe mixture refluxed for 3 hours
  2. dissolution(solids dissolved)
  3. temperatureThe solution is cooled to room temperature
  4. customThe volatiles are removed under vacuum
  5. additionTo the residue is added 100 ml of 2N NaOH
  6. temperatureThe mixture is refluxed overnight
  7. filtrationfiltered
  8. extractionThe solid is extracted with dichloromethane
  9. washthe extract is washed with 2N citric acid, water
  10. dry with materialdried (Na2SO4)
  11. customThe solvent is removed

Quellen und Nachweise

ORD-Eintrag
ord-36ed59aa81c14f2a9604ff13b4c5b93f
Quelldatensatz
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05849735

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