Triphenylphosphine → [(1-ethyl-1H-imidazol-4-yl)methyl](triphenyl)phosphonium chloride hydrochloride

HRID 2221659Notes

Reaction equation

HRID 2221659 reaction equation
[ClH:1].[Cl:2][CH2:3][C:4]1[N:5]=[CH:6][N:7]([CH2:9][CH3:10])[CH:8]=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:7]1[CH:8]=[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)[N:5]=[CH:6]1)[CH3:10]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 23076585HCID 23076585, compound

Product 1

HCID 86605746[(1-ethyl-1H-imidazol-4-yl)methyl](triphenyl)phosphonium chloride hydrochlorideYield 68.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloromethyl-1-ethyl-1H-imidazole hydrochloride (8.35 g), triphenylphosphine (12.1 g) and acetonitrile (200 mL) was heated under reflux for 16 hrs. After cooling, the obtained mixture was concentrated. Diethyl ether was added to the residue to allow crystallization, and the precipitated crystals were collected by filtration and washed successively with hexane and ethyl acetate. The obtained crystals were recrystallized from methanol-tetrahydrofuran to give [(1-ethyl-1H-imidazol-4-yl)methyl](triphenyl)phosphonium chloride hydrochloride as colorless crystals (14.09 g, yield 68%). melting point: 121-122° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hrs
  3. temperatureAfter cooling
  4. concentrationthe obtained mixture was concentrated
  5. additionDiethyl ether was added to the residue
  6. customcrystallization
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed successively with hexane and ethyl acetate
  9. customThe obtained crystals were recrystallized from methanol-tetrahydrofuran

Sources & evidence

ORD record
ord-3606228c5049442dabaaf8d891cbd8da
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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