Water → 1-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)-hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate

HRID 2188491Notes

Reaction equation

HRID 2188491 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][CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=[C:29]1[C:37]3[CH:38]=[CH:39][CH:40]=[C:35]4[C:36]=3[C:31](=[CH:32][CH:33]=[CH:34]4)[N:30]1[CH2:41][CH2:42][CH2:43][CH3:44])[CH:15]=[CH:16][CH:17]=2)[CH2:7][CH2:8][CH3:9].[F:45][C:46]([F:63])([S:59]([O-:62])(=[O:61])=[O:60])[CH:47]([O:52][C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[C:48]([F:51])([F:50])[F:49].[Na+].O>C(Cl)Cl>[F:63][C:46]([F:45])([S:59]([O-:62])(=[O:60])=[O:61])[CH:47]([O:52][C:53](=[O:58])[C:54]([CH3:56])([CH3:57])[CH3:55])[C:48]([F:49])([F:51])[F:50].[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][CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=[C:29]1[C:37]3[CH:38]=[CH:39][CH:40]=[C:35]4[C:36]=3[C:31](=[CH:32][CH:33]=[CH:34]4)[N:30]1[CH2:41][CH2:42][CH2:43][CH3:44])[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 866649641-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium perchlorate

Product 1

HCID 866649631-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)-hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.2 g (2 mmol) of 1-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium perchlorate, 6.1 g (3 mmol) of sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate aqueous solution, 10 g of water, and 25 g of methylene chloride was stirred overnight at room temperature, whereupon the organic layer was taken out. The organic layer was washed with water, concentrated in vacuum, combined with methyl isobutyl ketone, and concentrated in vacuum again. Diisopropyl ether was added to the residue for recrystallization. The crystal was collected and dried in vacuum, obtaining the target compound, 1-butyl-2-[7-(1-butyl-1H-benzo[cd]indol-2-ylidene)-hepta-1,3,5-trien-1-yl]-benzo[cd]indol-1-ium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate. Brown crystal, 2.0 g, yield 93%.

Workup

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

Sources & evidence

ORD record
ord-e9ae28b42d7042d39ec3aa1f2415d371
Source dataset
uspto-grants-2012_12
Patent number
US08323536B2

Reaction notes

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