Reaction #2320145

Reaction equation

2,3-Dichlorobenzamide

dimethylformamide dimethylacetal

→

title compound

2,3-dichloro-N-[(dimethylamino)methylene]benzamide

Conditions

Workup

1. 1
   Temperatureat reflux for 1.5 hours
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   Otherthe residue was partitioned between diethyl ether and water
4. 4
   WashThe organic phase was washed with water (2×), saturated sodium chloride
5. 5
   Dryingdried with sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationthe filtrate was concentrated under reduced pressure
8. 8
   OtherThe residue was purified by flash chromatography
9. 9
   Washeluting with ethyl acetate

Procedure

2,3-Dichlorobenzamide (4.96 g, 26.1 mmol) and dimethylformamide dimethylacetal (10 mL) were heated at reflux for 1.5 hours, allowed to cool to room temperature, concentrated under reduced pressure, and the residue was partitioned between diethyl ether and water. The organic phase was washed with water (2×), saturated sodium chloride, dried with sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate to provide the title compound. MS (DCI/NH3) m/z 245 (M+H)+.

Source