Hydrochloric Acid → N-[2-(Methylsulfanyl)ethyl]-4-nitroaniline

Participants

Reaction Conditions

Reaction Steps

2-aminoethanethiol dihydrochloride (45.4 g, 0.4 mol), water (100 mL), and 56.8 g (0.4 mol) of methyl iodide were mixed together. 16.5 g of sodium hydroxide pellets (0.4 mol) were dissolved in 100 mL of water and this solution was poured dropwise into the reaction mixture, while maintaining the temperature between 27-30° C. The resulting mixture was then stirred for 1 hour at 40° C. 21.2 g (10.2 mol) of para-fluoronitrobenzene and then 42 mL of triethylamine were added and the mixture was maintained in a boiling water bath for 3 hours. The resulting mixture was left overnight at room temperature and then acidified with hydrochloric acid and extracted with ethyl acetate. After evaporation to dryness, the 30 g of oil obtained were dissolved in 100 mL of 36% HCl. The resulting solution was extracted with ethyl ether to remove the starting material and, when cold, the aqueous phase was neutralized with aqueous ammonia. The resulting aqueous phase was extracted again with ethyl ether, dried, and evaporated to dryness to give 11 g of oil.

Provenance & Evidence