Water → 2-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-methylperhydroazepine

HRID 27423

Reaktionsgleichung

Reaktionsgleichung von HRID 27423
[Na].COS([O-])(=O)=O.CN(C)[C:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N+:11]=1[CH3:17].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:22][CH:21]=1.O>C(O)C.C(OCC)C>[CH2:30]([O:29][C:27]([C:26](=[C:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[CH3:17])[C:23]1[CH:22]=[CH:21][C:20]([Cl:19])=[CH:25][CH:24]=1)=[O:28])[CH3:31]

Komponenten

7

Edukt 4

HCID 962WaterHCID 84177Ethyl (4-chlorophenyl)acetateHCID 5360545SodiumHCID 178483040HCID 178483040, Verbindung

Produkt 1

HCID 539415482-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-methylperhydroazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Add (drop by drop at 90° in a stream of nitrogen to let the alcohol escape) a solution of 4.6 g of sodium in 100 ml of ethyl alcohol to a mixture of 53.2 g of the title compound of Example 1 and 29.8 g of ethyl 4-chlorophenylacetate. Stir it for a further 4 hours at 90° and then cool it to ambient temperature. Mix the cooled reaction mixture with 100 ml of water and 100 ml of diethyl ether, collect the organic phase and dry the latter over sodium sulfate. Concentrate the dried organic phase and then distil off any excess ethyl 4-chlorophenylacetate under a high vacuum to obtain a crude yield [15.5 g (34% of theory)] of the title compound as yellow oil.

Aufarbeitung

  1. additionAdd (drop by drop at 90° in a stream of nitrogen
  2. additionMix
  3. customcollect the organic phase
  4. dry with materialdry the latter over sodium sulfate
  5. concentrationConcentrate the dried organic phase
  6. customdistil off any excess ethyl 4-chlorophenylacetate under a high vacuum
  7. customto obtain a crude

Quellen und Nachweise

ORD-Eintrag
ord-ca593dee24784df38759aae09bcc0859
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221788

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