1,3-Dimethylimidazolium Iodide → HCID 73996930, compound

HRID 2164126Notes

Reaction equation

HRID 2164126 reaction equation
[I-].[CH3:2][N+:3]1[CH:7]=[CH:6][N:5]([CH3:8])[CH:4]=1.[CH:9]1[C:14]([C:15]2[O:19][C:18](/[CH:20]=[N:21]/[N:22]3[C:27](=[O:28])[NH:26][C:24](=[O:25])[CH2:23]3)=[CH:17][CH:16]=2)=[CH:13][CH:12]=[C:11]([N+:29]([O-:31])=[O:30])[CH:10]=1>CO>[CH3:2][N+:3]1[CH:7]=[CH:6][N:5]([CH3:8])[CH:4]=1.[N+:29]([C:11]1[CH:12]=[CH:13][C:14]([C:15]2[O:19][C:18]([CH:20]=[N:21][N:22]3[CH2:23][C:24](=[O:25])[NH:26][C:27]3=[O:28])=[CH:17][CH:16]=2)=[CH:9][CH:10]=1)([O-:31])=[O:30]

Participants

4

Reactant 2

HCID 203341,3-Dimethylimidazolium IodideHCID 69142737261-97-4

Product 1

HCID 73996930HCID 73996930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

An ion exchange column of Amberlite® IRA-410 resin (85 ml, 110 meq. on a 2.5 cm × 30 cm column) was activated by elution with 170 ml of 2N NaOH followed by washing with water to neutrality and then with 300 ml of methanol. A solution of 12.3 g (0.055 mole) of 1,3-dimethylimidazolium iodide (Part A) in 100 ml of methanol was placed on the basic anion exchange resin and eluted with methanol until the pH returned to neutral. The methanol solution of the quaternary hydroxide was collected in a flask containing 15.7 g (0.05 mole) of dantrolene suspended in 100 ml of methanol. The mixture was stirred for 60 min., then filtered. The methanol filtrate was concentrated in vacuo to dryness. The residue was triturated with 1000 ml of isopropanol and filtered, hot. The red-orange insoluble quaternary salt was then recrystallized from 100 ml of methanol, with Darco, to yield 12 g (53%), m.p. 172° -175° C.

Workup

  1. washAn ion exchange column of Amberlite® IRA-410 resin (85 ml, 110 meq. on a 2.5 cm × 30 cm column) was activated by elution with 170 ml of 2N NaOH
  2. washby washing with water to neutrality
  3. washeluted with methanol until the pH
  4. customThe methanol solution of the quaternary hydroxide was collected in a flask
  5. filtrationfiltered
  6. concentrationThe methanol filtrate was concentrated in vacuo to dryness
  7. customThe residue was triturated with 1000 ml of isopropanol
  8. filtrationfiltered
  9. customThe red-orange insoluble quaternary salt was then recrystallized from 100 ml of methanol, with Darco
  10. customto yield 12 g (53%), m.p. 172° -175° C.

Sources & evidence

ORD record
ord-3f93ebaae1954719a9e3dacf226df697
Source dataset
uspto-grants-1979_01
Patent number
US04137402

Reaction notes

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