Dimethyl Sulfide → 2-Amino-3-(methylthiomethyl)benzotrifluoride

Temperature

15 °C

Dimethylsulfide, 16 ml, was syringed all at once into a solution of 25.0 grams (g) of 2-(trifluoromethyl)aniline in 400 milliliters (ml) of methylene chloride. The reaction solution was cooled to 15° C. and 29.0 g of N-chlorosuccinimide was added in small portions over a 20 minute period at such a rate that the reaction temperature did not exceed 20° C. The reaction mixture was stirred at 15° C. for 15 minutes, then 30.4 ml of triethylamine was added dropwise over 15 minutes at such a rate that the temperature did not exceed 15° C. After an additional five minutes of stirring, the reaction was refluxed overnight, allowed to cool to room temperature, washed with two 200 ml portions of 10% sodium hydroxide, the organic phase separated, dried with magnesium sulfate and filtered. The remainder of the solvent was distilled off to yield 35.8 g of the crude desired product which was used without any additional purification in subsequent reactions.

1. customdid not exceed 20° C
2. customdid not exceed 15° C
3. stirringAfter an additional five minutes of stirring
4. temperaturethe reaction was refluxed overnight
5. temperatureto cool to room temperature
6. washwashed with two 200 ml portions of 10% sodium hydroxide
7. customthe organic phase separated
8. dry with materialdried with magnesium sulfate
9. filtrationfiltered
10. distillationThe remainder of the solvent was distilled off

ORD record

ord-01d898fbd0fe46c18676be97d5bcda83

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05500405