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A mixture of 29.7 g. (0.231 mole) of 4-fluorothiophenol, 41 g. (0.238 mole) of 2-chloro-5-nitroaniline and 14.9 g. (0.266 mole) of potassium hydroxide in 500 ml. of 95 percent aqueous ethanol is heated to its reflux temperature and maintained at reflux for one hour, then cooled with an ice bath. Some crude product is isolated as a solid by filtration, then the filtrate is diluted with water and extracted with four 300 ml. portions of chloroform. The combined extracts are washed with four 300 ml. portions of water and then with saturated sodium chloride solution and dried. Evaporation under vacuum provides a residue which is combined with the previously isolated crude solid product, 2-(4-fluorophenylthio)-5-nitroaniline. The solid is dissolved in 500 ml. of chloroform, then the solution is saturated with hydrogen chloride gas. The white precipitate which forms is separated by filtration, washed with chloroform and diethyl ether and dried to provide 2-(4-fluorophenylthio)-5-nitroaniline hydrochloride.

1. additionA mixture of 29.7 g
2. temperaturereflux temperature
3. temperaturemaintained
4. temperatureat reflux for one hour
5. temperaturecooled with an ice bath
6. customSome crude product is isolated as a solid by filtration
7. extractionextracted with four 300 ml
8. washThe combined extracts are washed with four 300 ml
9. dry with materialportions of water and then with saturated sodium chloride solution and dried
10. customEvaporation under vacuum
11. customprovides a residue which