Reacción #1973976

Ecuación de reacción

6-bromobenzo[d]thiazol-2-amine

hexane-2,5-dione

PPTS

water

→

title compound

Rendimiento 84.0%

6-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)benzo[d]thiazole

Rendimiento 84.0%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed with a Dean-Stark trap
2. 2
   workup.ADDITIONThe cooled mixture was poured into EtOAc (100 mL)
3. 3
   Extracciónextracted with saturated aq. NaHCO3 (2×100 mL) and brine
4. 4
   SecadoThe organic layer was dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude product was purified by column chromatography on silica gel using 9:1 EtOAc

Procedimiento

A solution 6-bromobenzo[d]thiazol-2-amine (5.75 g, 25.1 mmol), hexane-2,5-dione (2.95 mL, 25.1 mmol), and PPTS (0.95 g, 3.76 mmol) in benzene (100 ml) was refluxed for 16 h while water was removed with a Dean-Stark trap. The cooled mixture was poured into EtOAc (100 mL) and extracted with saturated aq. NaHCO3 (2×100 mL) and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 9:1 EtOAc:hexanes as the eluent to give the title compound as an orange oil (6.46 g, 84%).

Fuente