Reacción #696722

Ecuación de reacción

methyl iodide

Carbon disulfide

4-ethoxy-3-fluoroaniline

triethylamine

hydrochloric acid

→

methyl 4-ethoxy-3-fluorophenyldithiocarbamate

Rendimiento 58.8%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 10 hours
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 30 minutes
3. 3
   Extracciónfollowed by extraction with diethyl ether
4. 4
   LavadoThe organic layer was washed with a saturated sodium chloride solution
5. 5
   Secadodried with anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   LavadoThe residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=4:1)

Procedimiento

Carbon disulfide (2.0 g, 26 mmol) was added to a mixture of 4-ethoxy-3-fluoroaniline (2.7 g, 17 mmol) and triethylamine (4.0 g, 40 mmol) while stirring. The mixture was stirred at room temperature for 10 hours, N,N-dimethylformamide (30 ml) was added thereto and methyl iodide (2.2 g, 16 mmol) was added dropwise. The mixture was stirred at room temperature for 30 minutes and dilute hydrochloric acid was added thereto, followed by extraction with diethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=4:1) to obtain methyl 4-ethoxy-3-fluorophenyldithiocarbamate (2.5 g, 10 mmol) as crystals. m.p. 108.0° C.

Fuente