Imidazole → HCID 88254428, compound

HRID 377438Notes

Reaction equation

HRID 377438 reaction equation
Cl[CH2:2][CH2:3][P:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:18]([N:20]([CH2:23]C)[CH2:21]C)[CH3:19].[NH:25]1C=CN=C1.C[I:31]>C1(C)C=CC=CC=1.C(O)C>[I-:31].[CH3:21][N+:20]1[CH:18]=[CH:19][N:25]([CH2:2][CH2:3][P:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])[CH:23]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6328Methyl iodideHCID 8471TriethylamineHCID 1520891HCID 1520891, compound

Product 1

HCID 88254428HCID 88254428, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

13.2 g (49.9 mmol) of 2-chloro-1-diphenylphosphorylethane are, with addition of 7 ml (50 mmol) of triethylamine, reacted in a mixture of 50 ml of toluene and 30 ml of ethanol with 3.4 g (50 mmol) of imidazole. The mixture is refluxed for 5 hours. The resulting 1-imidazole-2-(diphenylphosphoryl)ethane is quaternized at room temperature with 3.13 ml (50 mmol) of methyl iodide. 1-methyl-3-(2-diphenylphosphorylethyl)imidazolium iodide is precipitated by addition of 100 ml of diethyl ether and dried under reduced pressure. This results in 15.7 g (65%) of (11a) as the monoethanol adduct.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. custom1-methyl-3-(2-diphenylphosphorylethyl)imidazolium iodide is precipitated by addition of 100 ml of diethyl ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-415b1195dbf44f0b8a673ff1299f997a
Source dataset
uspto-grants-2000_02
Patent number
US06025496

Reaction notes

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