1-Butanol → 1-{[1-(p-Chlorophenyl)cyclopropyl]methyl}-3-(2,6-dichlorobenzylideneamino)guanidine

HRID 2419790

Reaktionsgleichung

Reaktionsgleichung von HRID 2419790
I.[Cl:2][C:3]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:4]=1[CH:5]=[N:6][NH:7][C:8](=[NH:11])SC.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([CH2:27][NH2:28])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(O)CCC>O.C(OCC)(=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2([CH2:27][NH:28][C:8]([NH:7][N:6]=[CH:5][C:4]3[C:12]([Cl:16])=[CH:13][CH:14]=[CH:15][C:3]=3[Cl:2])=[NH:11])[CH2:25][CH2:26]2)=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 2631-ButanolHCID 4120166[1-(4-Chlorophenyl)cyclopropyl]methanamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Produkt 1

HCID 1785120881-{[1-(p-Chlorophenyl)cyclopropyl]methyl}-3-(2,6-dichlorobenzylideneamino)guanidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 7.80 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide and 4.37 g. of 1-(p-chlorophenyl)cyclopropanemethylamine in 100 ml. of n-butanol and 25 ml. of water is heated at reflux for 24 hours. The solution is cooled, diluted with water to a final volume of 2 liters and allowed to stand. Filtration gives a tan solid which is dissolved in ethyl acetate and purified by silica gel column chromatography. Crystallization of the product from diethyl ether gives the desired final product as colorless crystals, m.p. 126°-128° C.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. temperatureThe solution is cooled
  3. filtrationFiltration
  4. customgives a tan solid which
  5. custompurified by silica gel column chromatography
  6. customCrystallization of the product from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4944ab98b94743809047afb25af45334
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04107326

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