Reacción #2275674

ord-d7f5915dabd7442ea59fcfd7e9868533

Ecuación de reacción

CCCCn1c(=CC=C2CCC(C=CC3=[N+](CCCC)c4cccc5cccc3c45)=C2N(c2ccccc2)c2ccccc2)c2cccc3cccc1c32.[O-][Cl+3]([O-])([O-])[O-]
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
CC(C)(C)C(=O)OC(C(F)(F)F)C(F)(F)S(=O)(=O)[O-].[Na+]
sodium 1,1,3,3,3-pentafluoro-2-(pivaloyloxy)propanesulfonate
O
water
CC(C)(C)C(=O)OC(C(F)(F)F)C(F)(F)S(=O)(=O)[O-].CCCCn1c(=CC=C2CCC(C=CC3=[N+](CCCC)c4cccc5cccc3c45)=C2N(c2ccccc2)c2ccccc2)c2cccc3cccc1c32
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
Rendimiento 86.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThe organic layer was washed with water
  2. 2
    Concentraciónconcentrated in vacuum
  3. 3
    workup.ADDITIONDiisopropyl ether was added to the residue for recrystallization
  4. 4
    OtroThe crystal was collected
  5. 5
    Otrodried in vacuum

Procedimiento

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%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08323536B2uspto-grants-2012_12