Chloroform → 5,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

HRID 1762711

Reaktionsgleichung

Reaktionsgleichung von HRID 1762711
[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16]([NH2:18])=O)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH-].[Na+]>C(N(CC)CC)C>[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16]#[N:18])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 200417145,7-dihydro-6H-dibenz[c,e]azepine-6-carboxamide

Produkt 1

HCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 1.19 g of 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboxamide (see Example 10), 12 ml of chloroform, 2.7 ml of 50% sodium hydroxide solution and 50 mg of triethylamine is stirred at room temperature for 1 hour. The reaction mixture is then poured onto ice/water and the whole is extracted with methylene chloride. The extracts are washed with water, dried over anhydrous sodium sulphate and evaporated, and the residue is purified by flash chromatography on silica gel [eluent: n-hexane/ethyl acetate (9:1)]. There is obtained 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile, m.p. 118°-121° C.

Aufarbeitung

  1. additionThe reaction mixture is then poured onto ice/water
  2. extractionthe whole is extracted with methylene chloride
  3. washThe extracts are washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated
  6. customthe residue is purified by flash chromatography on silica gel [eluent: n-hexane/ethyl acetate (9:1)]

Quellen und Nachweise

ORD-Eintrag
ord-a2fecb493a334798b54ea121986c3cf8
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04833245

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