Triphenylphosphine → [(1-ethyl-1H-imidazol-5-yl)methyl](triphenyl)phosphonium chloride hydrochloride

HRID 2221656Notes

Reaction equation

HRID 2221656 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[N:8]([CH2:9][CH3:10])[CH:7]=[N:6][CH:5]=1.[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[ClH:2].[Cl-:1].[CH2:9]([N:8]1[C:4]([CH2:3][P+:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:5][N:6]=[CH:7]1)[CH3:10]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 229387405-(Chloromethyl)-1-Ethyl-1H-Imidazole Hydrochloride

Product 1

HCID 86605744[(1-ethyl-1H-imidazol-5-yl)methyl](triphenyl)phosphonium chloride hydrochlorideYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Chloromethyl-1-ethyl-1H-imidazole hydrochloride (6.00 g), triphenylphosphine (25.73 g) and acetonitrile (80 mL) were heated under reflux overnight. After cooling, the precipitated crystals were collected by filtration and washed with hexane to give [(1-ethyl-1H-imidazol-5-yl)methyl](triphenyl)phosphonium chloride hydrochloride as colorless crystals (10.50 g, yield 72%). melting point: 287-289° C.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with hexane

Sources & evidence

ORD record
ord-5b0c2ca112e24f53b51f9378c49f9e92
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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