Ethyl Acetate → N-[2-(1-cyclohexenyl)ethyl]-N'-(2-benzimidazolyl)thiourea

HRID 861608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861608
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[NH:10][C:11]([N:13]1[CH:17]=[CH:16]N=C1)=[S:12].[C:18]1(CCN)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1.C(OCC)(=O)C>CN(C)C=O>[C:18]1([CH2:16][CH2:17][NH:13][C:11]([NH:10][C:2]2[NH:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[S:12])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 769382-(1-Cyclohexenyl)ethylamineHCID 19704123N-(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide

Produkt 1

HCID 54139746N-[2-(1-cyclohexenyl)ethyl]-N'-(2-benzimidazolyl)thioureaAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-[(2-benzimidazolyl)thiocarbamoyl]imidazole (1.22 g, 5.0 mmol) and 2-(1-cyclohexenyl)ethylamine (0.64 g, 5.0 mmol) in N,N-dimethylformamide (20 mL) was stirred at 90° C. for 2 h. The reaction was cooled to room temperature, poured into ethyl acetate, washed with water, 1N aqueous HCl water, saturated sodium bicarbonate, and brine. The organic layer was concentrated and the resultant solid was crystallized from EtOAc to provide 0.82 g (55%) of the titled product as yellow needles:

Aufarbeitung

  1. washwashed with water, 1N aqueous HCl water, saturated sodium bicarbonate, and brine
  2. concentrationThe organic layer was concentrated
  3. customthe resultant solid was crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e807bedbb6e4422396ae278f91a805a6
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05714503

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