Water → 1-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)ethylidene]-2-(N,N-diphenylamino)cyclopent-1-en-1-yl)ethenyl)-benzo[cd]-indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propane-sulfonate

HRID 2188492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2188492
Cl([O-])(=O)(=O)=O.[CH2:6]([N+:10]1[C:18]2[C:13]3[C:14](=[CH:19][CH:20]=[CH:21][C:12]=3[C:11]=1[CH:22]=[CH:23][C:24]1[CH2:28][CH2:27][C:26](=[CH:29][CH:30]=[C:31]3[C:39]4[CH:40]=[CH:41][CH:42]=[C:37]5[C:38]=4[C:33](=[CH:34][CH:35]=[CH:36]5)[N:32]3[CH2:43][CH2:44][CH2:45][CH3:46])[C:25]=1[N:47]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH3:9].[F:60][C:61]([F:78])([S:74]([O-:77])(=[O:76])=[O:75])[CH:62]([O:67][C:68](=[O:73])[C:69]([CH3:72])([CH3:71])[CH3:70])[C:63]([F:66])([F:65])[F:64].[Na+].O>C(C(C)=O)C(C)C>[F:78][C:61]([F:60])([S:74]([O-:77])(=[O:75])=[O:76])[CH:62]([O:67][C:68](=[O:73])[C:69]([CH3:71])([CH3:72])[CH3:70])[C:63]([F:64])([F:66])[F:65].[CH2:6]([N+:10]1[C:18]2[C:13]3[C:14](=[CH:19][CH:20]=[CH:21][C:12]=3[C:11]=1[CH:22]=[CH:23][C:24]1[CH2:28][CH2:27][C:26](=[CH:29][CH:30]=[C:31]3[C:39]4[CH:40]=[CH:41][CH:42]=[C:37]5[C:38]=4[C:33](=[CH:34][CH:35]=[CH:36]5)[N:32]3[CH2:43][CH2:44][CH2:45][CH3:46])[C:25]=1[N:47]([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH3:9]

Komponenten

5

Edukt 3

HCID 962WaterHCID 86616368Sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonateHCID 866649661-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)ethylidene]-2-(N,N-diphenylamino)cyclopent-1-en-1-yl)ethenyl)-benzo[cd]indol-1-ium perchlorate

Produkt 1

HCID 866649651-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)ethylidene]-2-(N,N-diphenylamino)cyclopent-1-en-1-yl)ethenyl)-benzo[cd]-indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propane-sulfonateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 0.80 g (1 mmol) of 1-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)ethylidene]-2-(N,N-diphenylamino)cyclopent-1-en-1-yl)ethenyl)-benzo[cd]indol-1-ium perchlorate, 3.1 g (1.5 mmol) of sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate aqueous solution, 16 g of water, and 16 g of methyl isobutyl ketone was stirred overnight at room temperature, whereupon the organic layer was taken out. The organic layer was washed with water and concentrated in vacuum. Diisopropyl ether was added to the residue for recrystallization. The crystal was collected and dried in vacuum, obtaining the target compound, 1-butyl-2-(2-{3-[2-(1-butyl-1H-benzo[cd]indol-2-ylidene)ethylidene]-2-(N,N-diphenylamino)cyclopent-1-en-1-yl)ethenyl)-benzo[cd]-indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propane-sulfonate. Brown crystal, 0.88 g, yield 86%.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. concentrationconcentrated in vacuum
  3. additionDiisopropyl ether was added to the residue for recrystallization
  4. customThe crystal was collected
  5. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d7f5915dabd7442ea59fcfd7e9868533
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08323536B2

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