Reacción #79499

Ecuación de reacción

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one

methylene chloride

triethyloxonium tetrafluoroborate

p-chloroaniline

→

2-(4-chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one

Rendimiento 57.8%

Disolventes

water

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hr
2. 2
   ExtracciónThe separated oil was extracted with chloroform
3. 3
   SecadoThe chloroform layer was dried over anhydrous magnesium sulfate
4. 4
   Otrothe solvent was evaporated under reduced pressure
5. 5
   OtroThe residue was purified by column chromatography (chloroform-n-hexane, 1/1)

Procedimiento

5-Methyl-5-phenyl-3-phenylamino-2-thioxothiazolidin-4-one (0.28 g) was mixed with a 1M methylene chloride solution of triethyloxonium tetrafluoroborate (1 ml) at room temperature. The reaction mixture was stirred for 24 hrs at room temperature then p-chloroaniline (0.25 g) in chloroform (10 ml) was added to the mixture at 0° C. The mixture was stirred at room temperature for 1 hr and then water was added. The separated oil was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform-n-hexane, 1/1) to yield 2-(4-chlorophenyl)imino-5-methyl-5-phenyl-3-phenylaminothiazolidin-4-one (0.21 g) having a melting point of 53-54° C.

Fuente