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1,3-Dimethylimidazolium Iodide → HCID 73996930, Verbindung

HRID 2164126
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2164126
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 203341,3-Dimethylimidazolium IodideHCID 6914273Dantrolene

Produkt 1

HCID 73996930HCID 73996930, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-3f93ebaae1954719a9e3dacf226df697
Quelldatensatz
uspto-grants-1979_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04137402

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