Iodoethane → 9-Ethyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide

HRID 602566

Reaktionsgleichung

Reaktionsgleichung von HRID 602566
[CH3:1][C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][CH:3]=1.[I:14][CH2:15][CH3:16]>CC(C)=O>[I-:14].[CH2:15]([N+:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]2[C:2]([CH3:1])=[CH:3][S:4][C:5]=12)[CH3:16]

Komponenten

4

Edukt 2

HCID 6340IodoethaneHCID 8282853-Methyl[1,3]thiazolo[3,2-a]benzimidazole

Produkt 1

HCID 450275779-Ethyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

153 mg of 3-methyl[1,3]thiazolo[3,2-a]benzimidazole were solubilised in acetone (5 mL). Then 328 μl, (5 eq) of iodoethane were added and the solution stirred under reflux. After 18 h, 9-ethyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide was recovered as a white powder (267 mg, 96%) by filtration. Mp 268° C.; 1H NMR (300 MHz, MeOD) δ=1.64 (3H, t, J=7.3, CH3), 2.95 (3H, d, J=CH3), 4.66 (2H, q, J=7.3, CH2), 7.37 (1H, q, J=1.3, H5), 7.66-7.81 (2H, m, Ar), 8.01-8.04 (1H, m, Ar), 8.27-8.30 (1H, m, Ar); 13C NMR (75 MHz, MeOD) δ=13.21, 14.25, 43.61, 112.19, 113.66, 114.93, 126.26, 128.32, 129.05, 135.29, 137.28, 155.62.

Aufarbeitung

  1. temperatureunder reflux
  2. filtration9-ethyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide was recovered as a white powder (267 mg, 96%) by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d2f94d58b9654daab1d4639f5ff291d5
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906541B2

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