Water → N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1H-indole-3-ethanamine

HRID 2419139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2419139
[I-].[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N+](C)C3C=CC=CC=3)[S:9][C:5]=2[CH:4]=1.Cl.[NH2:21][CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N:21][CH2:22][CH2:23][C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)[S:9][C:5]=2[CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 67652Tryptamine hydrochlorideHCID 203138445-Chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide

Produkt 1

HCID 20313872N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1H-indole-3-ethanamineAusbeute 12,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide (8.39g), tryptamine hydrochloride (3.94g) and anhydrous sodium carbonate (2.12g) in 300 ml of anhydrous dimethylformamide is heated at 130° C under a nitrogen atmosphere for 3 hours. After this time the reaction mixture is poured into 1 liter of water and extracted with three 300 ml portions of benzene. The combined benzene extracts are dried over anhydrous sodium sulfate and then concentrated in vacuo to yield an oil. This oil is chromatographed on 600 ml of silica gel eluting first with dichloromethane/pentane (1:1) and finally dichloromethane. The resultant product with Rf =0.36 (silica gel/dichloromethane) is recrystallized from dichloromethane/pentane to yield 840 mg of the title compound, melting point 145°-147° C.

Aufarbeitung

  1. extractionextracted with three 300 ml portions of benzene
  2. dry with materialThe combined benzene extracts are dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto yield an oil
  5. customThis oil is chromatographed on 600 ml of silica gel eluting first with dichloromethane/pentane (1:1) and finally dichloromethane
  6. customThe resultant product with Rf =0.36 (silica gel/dichloromethane) is recrystallized from dichloromethane/pentane

Quellen und Nachweise

ORD-Eintrag
ord-7a15f652bec54ceaaeda07641b9ba9af
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04104467

Notizen zur Reaktion

Wird geladen…