Réaction #56595

ord-92f36e32dd5d4bacbd6092f3ab38af0a

Équation de réaction

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
Rendement 84.4%

Solvants

Conditions de réaction

Température
60°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureAfter cooling to room temperature the reaction mixture
  2. 2
    Autrewas quenched with 100 ml 3N HCl
  3. 3
    Filtrationthe resulting precipitate was filtered off
  4. 4
    Lavagewashed with water (100 ml) and ethanol (50 ml)

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07419620B2uspto-grants-2008_09