Reacción #833508

ord-07e12ebad1c0464f8db6a0c195f5d008

Ecuación de reacción

CN(C)c1ccc(N=Nc2nccs2)cc1
N,N-dimethyl-4-[1,3-thiazol-2-yldiazenyl]aniline
O=S1(=O)CCCCO1
butane sultone
CN(C)c1ccc(N=Nc2scc[n+]2CCCCS(=O)(=O)[O-])cc1
4-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate
Rendimiento 87.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling
  2. 2
    Filtraciónthe precipitated product is filtered off
  3. 3
    Lavadowashed with acetone
  4. 4
    Otrodried
  5. 5
    OtroThe dye is recrystallized with methanol/ethyl acetate

Procedimiento

8.5 g (36.6 mmol) of N,N-dimethyl-4-[1,3-thiazol-2-yldiazenyl]aniline are heated with 85 ml of butane sultone at 110° C. for 6 hours. After cooling, 200 ml of tetrahydrofuran are added to the reaction mixture and the precipitated product is filtered off, washed with acetone and dried. The dye is recrystallized with methanol/ethyl acetate. 11.8 g (87% of theory) of 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate are obtained as a dark blue power.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07393366B2uspto-grants-2008_07