Triethylamine → 2-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetyl Azide

HRID 67641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 67641
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([CH2:15][C:16](O)=[O:17])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>O1CCCC1.O.C(OCC)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH:6]([CH2:15][C:16]([N:34]=[N+:35]=[N-:36])=[O:17])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 205274972-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic Acid

Produkt 1

HCID 205274942-Chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetyl Azide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a magnetically stirred, ice cold solution of 2-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid (20.0 g, described in Example 2) in dry tetrahydrofuran (400 ml) is added, under an atmosphere of dry nitrogen, triethylamine (13 ml) and ethyl chloroformate (11.6 g). After stirring for 1 hr at 0° C., the suspension is cooled to -10° C. and a solution of sodium azide (6.4 g) in distilled water (40 ml) is added. After stirring for a further 1 hr at -10° C., the reaction mixture is diluted with diethyl ether (200 ml). The organic phase is dried over magnesium sulfate and evaporated to give the title compound.

Aufarbeitung

  1. stirringAfter stirring for 1 hr at 0° C.
  2. stirringAfter stirring for a further 1 hr at -10° C.
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8351b839dccc4aec8ac725de4ee6eb88
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346090

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