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 2188492Notes

Reaction equation

HRID 2188492 reaction equation
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]

Participants

5

Reactant 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

Product 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-sulfonateYield 86%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-d7f5915dabd7442ea59fcfd7e9868533
Source dataset
uspto-grants-2012_12
Patent number
US08323536B2

Reaction notes

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