Ethyl Acetate → N-[2-(2,6-difluorophenyl)ethyl]-N'-(2-pyridyl)thiourea

HRID 233716Notes

Reaction equation

HRID 233716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH2:11].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](N1C=CN=C1)=[S:20].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][NH:11][C:19]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)=[S:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 37461112-(2,6-Difluorophenyl)ethan-1-amineHCID 197041381-[(2-Pyridyl)thiocarbamoyl]imidazole

Product 1

HCID 3001258N-[2-(2,6-difluorophenyl)ethyl]-N'-(2-pyridyl)thioureaYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2,6-difluorophenyl)ethylamine (0.43 g, 2.7 mmol) and 1-[(2-pyridyl)thiocarbamoyl]imidazole (0.55 g, 2.7 mmol) in N,N-dimethylformamide (20 mL) was stirred at 90° C. for 27 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 0.08 g (10%) of the titled product as a pale 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-6dfae7d4faa7442dbd962814b3a2691d
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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