1,1'-Thiocarbonyldiimidazole → 1-[(2-(2,6-Difluorophenyl)ethyl)thiocarbamoyl]imidazole

HRID 861612Notes

Reaction equation

HRID 861612 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1CCN>C(#N)C>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=1[CH2:11][CH2:12][NH:8][C:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 37461112-(2,6-Difluorophenyl)ethan-1-amine

Product 1

HCID 152056241-[(2-(2,6-Difluorophenyl)ethyl)thiocarbamoyl]imidazoleYield 124.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,1'-thiocarbonyldiimidazole (9.5 g, 48 mmol) and 2-(2,6-difluorophenyl)ethylamine (7.54 g, 48 mmol) in acetonitrile (100 mL) was stirred at room temperature for 20 h. The solution was concentrated under reduced pressure and the resulting precipitate was collected by filtration and triturated with hexane to provide 16 g of crude titled product as a brown solid:

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. filtrationthe resulting precipitate was collected by filtration
  3. customtriturated with hexane

Sources & evidence

ORD record
ord-02667c8ff85d4eceac3f39333387eb3e
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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