Diethyl Ether → 3-(3,5-Dinitrobenzyl)-2-methyl-1,3-benzothiazol-3-ium iodide

HRID 2306535

Reaktionsgleichung

Reaktionsgleichung von HRID 2306535
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[CH2:17][I:18])([O-:13])=[O:12].CCOCC>CC(C)=O>[I-:18].[N+:11]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[CH2:17][N+:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]=1[CH3:1])([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 84462-MethylbenzothiazoleHCID 226090731-(Iodomethyl)-3,5-dinitrobenzene

Produkt 1

HCID 226090303-(3,5-Dinitrobenzyl)-2-methyl-1,3-benzothiazol-3-ium iodideAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-methylbenzothiazole (3 ml, 20.1 mmol) was dissolved in acetone (25 ml), to which was added 3,5-dinitrobenzyl iodide (7.4 g, 24.1 mmol) and heated with stirring to reflux for 15 hours. The reaction was allowed to cool and added drop-wise to ether (500 ml) to produce a fine yellow solid which was filtered and dried to constant weight in vacuo to give 3-(3,5-dinitrobenzyl)-2-methyl-1,3-benzothiazol-3-ium iodide (5 g, 10.9 mmol, 45% yield). MS: m/z=328 (C15H12N3O4S=330.3). 1H NMR (200 MHz-DMSO-d6): δ 2.85 (s, 1 H); 3.7 (s, 3H); 6.35 (s, 2H); 7.37 (m, 2H); 8.23 (d, 1H); 8.53 (d, 1H); 8.62 (s, 2H): 8.8 (s, 1H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 15 hours
  3. temperatureto cool
  4. customto produce a fine yellow solid which
  5. filtrationwas filtered
  6. customdried to constant weight in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0e4f8b3195c445fab058e0ce63bbe959
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06828116B1

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