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

HRID 233717Notes

Reaction equation

HRID 233717 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-f9599652d4ff4e9fb0257b9743d8df4c
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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