Reacción #56595

ord-92f36e32dd5d4bacbd6092f3ab38af0a

Ecuación de reacción

CN(C)c1ccc(N=Nc2ccc(N=Nc3ccc(O)c4ccccc34)cc2)c2ccccc12
1-[4-(4-(dimethylamino)naphthylazo)phenylazo]-4-hydroxy-naphtalene
C=CC(=O)OCCCCCCI
6-iodohexyl acrylate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
C=CC(=O)OCCCCCCOc1ccc(N=Nc2ccc(N=Nc3ccc(N(C)C)c4ccccc34)cc2)c2ccccc12
1-[4-(4-(dimethylamino)naphthylazo)-phenylazo]-4-(6-acryloyloxyhexyloxy)naphtalene
Rendimiento 84.4%

Disolventes

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling to room temperature the reaction mixture
  2. 2
    Otrowas quenched with 100 ml 3N HCl
  3. 3
    Filtraciónthe resulting precipitate was filtered off
  4. 4
    Lavadowashed with water (100 ml) and ethanol (50 ml)

Procedimiento

A mixture consisting of 0.44 g of 1-[4-(4-(dimethylamino)naphthylazo)phenylazo]-4-hydroxy-naphtalene, 0.56 g of 6-iodohexyl acrylate, and 0.28 g of potassium carbonate in 10 ml of DMF was stirred under nitrogen atmosphere for 3 h at 60° C. After cooling to room temperature the reaction mixture was quenched with 100 ml 3N HCl and the resulting precipitate was filtered off, washed with water (100 ml) and ethanol (50 ml) to give 0.5 g of pure 1-[4-(4-(dimethylamino)naphthylazo)-phenylazo]-4-(6-acryloyloxyhexyloxy)naphtalene as a brownish powder; λmax. (CB 483): 504 nm.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07419620B2uspto-grants-2008_09