Reacción #2122518

ord-d9cd9d2e624a4c66bef0ac8371f0caa3

Ecuación de reacción

CCCCCCN(CCCCCC)S(=O)(=O)c1ccc2nc(C)sc2c1
Compound 20
CCCCCCN(CCCCCC)S(=O)(=O)c1ccc2nc(C)sc2c1
N,N-dihexyl-2-methylbenzo[d]thiazole-6-sulfonamide
COS(=O)(=O)c1ccc(C)cc1
p-toluenesulfonic acid methyl ester
CCCCCC
hexane
CCCCCCN(CCCCCC)S(=O)(=O)c1ccc2c(c1)sc(C)[n+]2C.Cc1ccc(S(=O)(=O)[O-])cc1
Compound 21
Rendimiento 78.9%
CCCCCCN(CCCCCC)S(=O)(=O)c1ccc2c(c1)sc(C)[n+]2C.Cc1ccc(S(=O)(=O)[O-])cc1
6-(N,N-dihexylsulfamoyl)-2,3-dimethylbenzo[d]-thiazole-3-ium tosylate
Rendimiento 78.9%

Disolventes

Condiciones de reacción

Temperatura
130°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturato cool to room temperature
  2. 2
    OtroA sticky dark brown solid separated which
  3. 3
    Lavadowas washed with hexane
  4. 4
    Otrodried under vacuum

Procedimiento

A mixture of Compound 20 (2.0 g, 5.0 mmol) and p-toluenesulfonic acid methyl ester (1.4 g, 7.5 mmol) was heated in a pressure tube at 130° C. for 2 hours. The mixture was allowed to cool to room temperature, and the resulting mass was dissolved in ethyl acetate (4 ml). The combined mixture was then added drop wise to hexane (40 ml). A sticky dark brown solid separated which was washed with hexane and dried under vacuum to yield 2.3 g (78%) of Compound 21 which was used without any further purification. The structure of this compound is given below:

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08574881B2uspto-grants-2013_11