Reacción #1867190

Ecuación de reacción

N-(1',1'-dimethylpropynyl)-3,5-dichlorobenzamide

methylene chloride

chlorine

pyridine

→

2-(3',5'-dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothis solution was washed with aqueous sodium sulfite
2. 2
   Otrothe solvent was removed
3. 3
   OtroThe white solid obtained
4. 4
   Filtraciónfiltered
5. 5
   Otroto remove solids
6. 6
   LavadoThe mother liquor was washed sequentially with cold 1% hydrochloric acid (25 ml), sodium bicarbonate (50 ml), water and brine
7. 7
   OtroThe solvent was removed
8. 8
   Secadoafter drying over magnesium sulfate

Procedimiento

N-(1',1'-dimethylpropynyl)-3,5-dichlorobenzamide (25 gm, 0.096 m) was dissolved in methylene chloride (300 ml) and excess chlorine (2.5-3 equivalents) was bubbled through this solution at room temperature. After the starting material had disappeared (as indicated by thin layer chromatography, TLC), this solution was washed with aqueous sodium sulfite and the solvent was removed. The white solid obtained was slurried in ether (250 ml) and pyridine (8.0 gm) was added. The mixture was stirred for about 1 hour and then filtered to remove solids. The mother liquor was washed sequentially with cold 1% hydrochloric acid (25 ml), sodium bicarbonate (50 ml), water and brine. The solvent was removed after drying over magnesium sulfate and 28 gm of 2-(3',5'-dichlorophenyl)-4,4-dimethyl-5-chloro-5-dichloromethyloxazoline was obtained.

Fuente