2-ethylsulfanylaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 500 mg of 2-nitro-4-trifluoromethylbenzaldehyde, 349 mg of 2-(ethylsulfanyl)aniline and 4 ml of toluene was refluxed for 4 hours and then concentrated under reduced pressure. The resulting residue was washed with t-butyl methyl ether to obtain 777 mg of (2-ethylsulfanylphenyl) (2-nitro-4-trifluoromethylbenzylidene)amine. was refluxed for 4 hours concentrated under reduced pressure The resulting residue was washed with t-butyl methyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under conditions similar to those used for the preparation of 2-(ethylthio)aniline in Example 2, 2-amino-5-fluorothiophenol was alkylated with methyl iodide to give 2-methylthio-4-fluoroaniline.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Aminothiophenol (5.0 g, 40 mmol, Lancaster Synthesis Inc., Windham, N.H.) was stirred in dry ethanol (100 mL) and cooled in an ice bath. Potassium t-butoxide (4.5 g, 40 mmol) was added portionwise over 15 minutes and the mixture was stirred for an additional 45 minutes. Ethyl iodide (3.3 mL, 41 mmol) was added dropwise over 15 minutes and the mixture was allowed to warm to room temperature and stirred for 45 minutes. The mixture was filtered and the filtrate evaporated to dryness in vacuo. The resulting residue was treated with dichloromethane (100 mL) and filtered and the resulting filtrate was evaporated to dryness in vacuo to give 2-(ethylthio)aniline (5.2 g). cooled in an ice bath stirred for 45 minutes The mixture was filtered the filtrate evaporated to dryness in vacuo The resulting residue was treated with dichloromethane (100 mL) filtered the resulting filtrate was evaporated to dryness in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 500 mg of 2-nitro-4-trifluoromethylbenzaldehyde, 349 mg of 2-(ethylsulfanyl)aniline and 4 ml of toluene was refluxed for 4 hours and then concentrated under reduced pressure. The resulting residue was washed with t-butyl methyl ether to obtain 777 mg of (2-ethylsulfanylphenyl) (2-nitro-4-trifluoromethylbenzylidene)amine. was refluxed for 4 hours concentrated under reduced pressure The resulting residue was washed with t-butyl methyl ether