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

HRID 861610Notes

Reaction equation

HRID 861610 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-b3efeeeb8ff14fb6bea30ac64e155b5f
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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