Ammonium hexafluorophosphate → 3-Benzyl-1-methoxy-4,5-dimethylimidazolium hexafluorophosphate

HRID 1072768Notes

Reaction equation

HRID 1072768 reaction equation
[I-].[CH2:2]([N:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[N+:11]([O:16][CH3:17])=[CH:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:18][P-:19]([F:24])([F:23])([F:22])([F:21])[F:20].[NH4+]>O>[F:18][P-:19]([F:24])([F:23])([F:22])([F:21])[F:20].[CH2:2]([N:9]1[C:13]([CH3:14])=[C:12]([CH3:15])[N+:11]([O:16][CH3:17])=[CH:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 9793912Ammonium hexafluorophosphateHCID 178502610HCID 178502610, compound

Product 1

HCID 1785026093-Benzyl-1-methoxy-4,5-dimethylimidazolium hexafluorophosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Crude iodide 2 was taken up in deionized (DI) water, which separated the product from small amounts of a dark, insoluble residue. The water solution was decanted to a second flask and a solution of ammonium hexafluorophosphate (950 mg, ca. 5.8 mmol) in 10 mL of DI water was added in portions. An oil separated during the addition, and the supernatant solution was decanted out. The oil was crushed in cold (0° C.), and subsequently recrystallized in methanol. Yield: 1.3 g (73% from 1). 1H-NMR (δ, CDCl3): 8.67 (s, 1H, N—CH—N); 7.39 (m, 3H, C6H5); 7.29 (d, 2H, C6H5); 5.24 (s, 2H, NCH2); 4.21 (s, 3H, OCH3); 2.27 (s, 3H, CH3); 2.17 (s, 3H, CH3).

Workup

  1. customseparated the product from small amounts of a dark, insoluble residue
  2. customThe water solution was decanted to a second flask
  3. customAn oil separated during the addition
  4. customthe supernatant solution was decanted out
  5. customThe oil was crushed in cold (0° C.)
  6. customsubsequently recrystallized in methanol

Sources & evidence

ORD record
ord-6b368fc424bb42e48e1214a6f2742362
Source dataset
uspto-grants-2005_06
Patent number
US06911546B2

Reaction notes

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