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

HRID 895798Notes

Reaction equation

HRID 895798 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-5acde108e6544fa1b38560c762ce4f9f
Source dataset
uspto-grants-2005_07
Patent number
US06916936B2

Reaction notes

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