Reacción #90351

Ecuación de reacción

isocyanate

3,5-dimethylaniline

cesium carbonate

3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine

sodium bicarbonate

triphosgene

→

1-(3,5-dimethylphenyl)-3-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)urea

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónat a concentration between about 0.01 M to about 1 M)
2. 2
   OtroThe reaction
3. 3
   Otromay be placed in an ice bath
4. 4
   OtroThe reaction
5. 5
   Otroupon which the reaction
6. 6
   Filtraciónfiltered through a phase separator
7. 7
   Concentraciónconcentrated
8. 8
   Otrocompletion of the reaction
9. 9
   Otrothe product may be obtained
10. 10
    Otroorganic chemistry techniques of workup and purification

Procedimiento

To 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine (1 equiv) and sodium bicarbonate (5 equiv) in an appropriate reaction vessel may be added a solvent such as dichloromethane (at a concentration between about 0.01 M to about 1 M). The reaction may be placed in an ice bath and triphosgene (0.4 equiv) can be added in one portion. The reaction may be monitored by LC/MS to observe formation of the isocyanate, upon which the reaction may be diluted with dichloromethane, filtered through a phase separator, and concentrated. The residue may be suspended in a solvent such as acetonitrile (0.1 M to about 1 M), followed by addition of 3,5-dimethylaniline (1.0-1.5 equiv) and cesium carbonate (1.0-1.5 equiv). Following completion of the reaction, the product may be obtained using standard organic chemistry techniques of workup and purification.

Fuente