Potassium Iodide → HCID 178436205, Verbindung

HRID 991594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 991594
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:15]=1[CH2:16]Cl)[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(COC)OC>[CH2:12]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:15]=1[CH2:16][NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:13]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 178432166HCID 178432166, Verbindung

Produkt 1

HCID 178436205HCID 178436205, VerbindungAusbeute 27,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

4-amino-2-methylbenzimidazole (0.4 g, 2.7 mmol) and 2-ethyl-6-methylbenzylchloride (0.46 g, 2.7 mmol) were dissolved in 10 ml dimethoxyethane. Sodium carbonate (0.5 g, 4.7 mmol) and (0.2 g, 4.7 mmol) of potassium iodide were added to the solution. The reaction mixture was refluxed to for 2 h. Inorganic salts were removed by filtration and washed with dimethoxyethane. The filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel. The product was eluted with a 50:50 mixture of methylene chloride and ethyl acetate. There was obtained 0.21 g of the title compound. (1H-NMR, 400 MHz, CDCl3): 1.1 (t, 3H), 2.35 (s, 3H), 2.45 (s, 3H), 2.70 (q, 2H), 4.35 (s, 2H), 4.45 (bs, 1H), 6.55 (d, 1H), 6.75 (d, 1H), 6.95-7.20 (m, 4H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed to for 2 h
  2. customInorganic salts were removed by filtration
  3. washwashed with dimethoxyethane
  4. customThe filtrate was evaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel
  6. washThe product was eluted with a 50:50 mixture of methylene chloride and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cea66ba7e60a41dab5fb79c2bf79053c
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06465505B1

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