Reacción #2045097

Ecuación de reacción

water

pyrrol

5-chloro-1,2,4-thiadiazole

5-chloro-3-(4-chlorophenyl)-1,2,4-thiadiazole

Sodium hydride

→

3-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1,2,4-thiadiazole

Rendimiento 45.0%

Disolventes

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated for 18 h to 55° C. ext
2. 2
   Temperaturawas heated to 100° C. ext
3. 3
   workup.WAITtemperature for 6 h
4. 4
   Otroisolated by filtration
5. 5
   OtroThe purification by column chromatography (SiO2, 0-10% ethyl acetate inheptanes)

Procedimiento

The 5-chloro-1,2,4-thiadiazole compound (102 mg, 0.445 mmol) was dissolved in DMSO (2 mL) and pyrrol (300 mg, 2.22 mmol) added at room temperature. The mixture was heated for 18 h to 55° C. ext. temperature, however no conversion was found (sample tested by 1H-NMR). Sodium hydride (55% wetted with mineral oil, 20 mg, 0.467 mmol) was added and the mixture heated to 80° C. ext. temperature for 5 h. As the conversion was not complete (sample tested by 1H-NMR) the mixture was heated to 100° C. ext. temperature for 6 h. The reaction mixture was poured into water (10 mL) and crude product isolated by filtration. The purification by column chromatography (SiO2, 0-10% ethyl acetate inheptanes) afforded 3-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1,2,4-thiadiazole (52 mg, 0.199 mmol, 45%), which was 98% pure (HPLC 254 nm). 1H-NMR spectra is in accordance with the chemical structure.

Fuente