Ethyl Acetate → N-[2-(2-Chlorophenyl)ethyl]-N'-pyridin-2-ylthiourea

HRID 2257795Notes

Reaction equation

HRID 2257795 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([N:10]1[CH:14]=[CH:13]N=C1)=[S:9].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1CCN.C(OCC)(=O)C>CN(C)C=O>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:13][CH2:14][NH:10][C:8]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[S:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 831172-(2-Chlorophenyl)ethylamineHCID 197041381-[(2-Pyridyl)thiocarbamoyl]imidazole

Product 1

HCID 19703888N-[2-(2-Chlorophenyl)ethyl]-N'-pyridin-2-ylthioureaYield 14.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-pyridyl)thiocarbamoyl] imidazole (1.02 g, 5.0 mmol) and 2-(2-chlorophenyl)ethylamine (0.81 g, 5.0 mmol) in N,N-dimethylformamide (20 mL) was stirred at 90° C. for 24 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 oil was purified by chromatography on silica gel to provide 0.21 g (14%) of the titled product as a yellow solid:

Workup

  1. washwashed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine
  2. concentrationThe organic layer was concentrated
  3. customthe resultant oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f28fdf09710940f8a1cd472de55dd5eb
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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