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

HRID 861608Notes

Reaction equation

HRID 861608 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-e807bedbb6e4422396ae278f91a805a6
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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