Réaction #2122518

ord-d9cd9d2e624a4c66bef0ac8371f0caa3

Équation de réaction

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
Rendement 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
Rendement 78.9%

Conditions de réaction

Température
130°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températureto cool to room temperature
  2. 2
    AutreA sticky dark brown solid separated which
  3. 3
    Lavagewas washed with hexane
  4. 4
    Autredried under vacuum

Mode opératoire

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:

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08574881B2uspto-grants-2013_11