1-Methylimidazole → HCID 86655189, compound

HRID 874173Notes

Reaction equation

HRID 874173 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[F:7][C:8]([F:18])([F:17])[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][Br:13].C(OCC)C>ClCCCl>[Br-:13].[CH3:1][N+:2]1[CH:6]=[CH:5][N:4]([CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[C:9]([C:8]([F:7])([F:17])[F:18])[CH:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 3283Diethyl EtherHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzene

Product 1

HCID 86655189HCID 86655189, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 25 ml one-necked flask, 1.4 g (17.05 mmol) of 1-methylimidazole are dissolved in 15 ml of 1,2-dichloroethane and then 4.89 g (20.46 mmol) of 3-trifluoromethylbenzyl bromide are added. After heating overnight at 80°, 50 ml of diethyl ether are added. The oil, which is then separated by decantation, is crystallized from a mixture of ethyl acetate and tetrahydrofuran (2/1 by volume). The crystals thus obtained are drained and then dried under reduced pressure. 3.06 g (56%) of 1-methyl-3-(3-trifluoromethylbenzyl)imidazolium bromide are thus obtained in the form of off-white crystals, used as they are in the next step, whose characteristic is the following:

Workup

  1. temperatureAfter heating overnight at 80°
  2. customThe oil, which is then separated by decantation
  3. customis crystallized from a mixture of ethyl acetate and tetrahydrofuran (2/1 by volume)
  4. customThe crystals thus obtained
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d34e150d5d8643a5a85e45028fa42de6
Source dataset
uspto-grants-2015_03
Patent number
US08980875B2

Reaction notes

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