4-Nitrobenzyl chloride → 3-Methyl-9-(4-nitrobenzyl)[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride

HRID 602572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602572
[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.[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][Cl:22])=[CH:19][CH:18]=1)([O-:16])=[O:15]>CC(C)=O>[Cl-:22].[CH3:1][C:2]1[N:9]2[C:5](=[N+:6]([CH2:21][C:20]3[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=3)[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 74824-Nitrobenzyl chlorideHCID 8282853-Methyl[1,3]thiazolo[3,2-a]benzimidazole

Produkt 1

HCID 866417073-Methyl-9-(4-nitrobenzyl)[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

204 mg of 3-methyl[1,3]thiazolo[3,2-a]benzimidazole were solubilised in acetone (3 mL). Then 558 mg (3 eq) of 4-nitrobenzyl chloride were added and the solution stirred under reflux. After 18 h, 3-methyl-9-(4-nitrobenzyl)[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride was recovered as a pale yellow powder (363 mg, 94%) by filtration. Mp 241° C.; 1H NMR (300 MHz, MeOD) δ=2.95 (3H, d, J=1.3, CH3), 5.97 (2H, s, CH2), 7.30 (1H, q, J=1.3, H5), 7.68-7.82 (4H, m, Ar), 7.96-8.03 (1H, m, Ar), 8.27-8.36 (3H, m, Ar); 13C NMR (75 MHz, MeOD) δ=14.11, 50.56, 112.76, 113.82, 115.08, 125.37 (2C), 126.63, 128.64, 129.12, 131.04 (2C), 135.43, 137.72, 140.44, 149.92, 156.37; HRMS m/z C17H14N3O2S [M−Cl]− calcd: 324.0801, found: 324.0802.

Aufarbeitung

  1. temperatureunder reflux
  2. filtration3-methyl-9-(4-nitrobenzyl)[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride was recovered as a pale yellow powder (363 mg, 94%) by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c5ca3df5a1d543e986e28b7f2fe153c9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906541B2

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