Reaction #696722

Reaction equation

methyl iodide

Carbon disulfide

4-ethoxy-3-fluoroaniline

triethylamine

hydrochloric acid

→

methyl 4-ethoxy-3-fluorophenyldithiocarbamate

Yield 58.8%

Solvents

N,N-dimethylformamide

Conditions

Workup

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
   Extractionfollowed by extraction with diethyl ether
4. 4
   WashThe organic layer was washed with a saturated sodium chloride solution
5. 5
   Dryingdried with anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   WashThe residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate=4:1)

Procedure

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.

Source