Hydrochloric Acid → 2-{4-[(Trifluoromethyl)sulfanyl]phenyl}ethan-1-amine

4-(Trifluoromethylthio)phenylacetonitrile (183.4 mg, 0.844 mmol), 0.3 molar in THF, was heated to reflux and then treated with Borane-methyl sulfide complex (88.09 μL, 0.929 mmol). After 1 hour of refluxing, the reaction mixture was cooled to ambient temperature and then treated dropwise with 5.0 molar hydrochloric acid (607.9 μL, 3.040 mmol). The reaction mixture was then heated to reflux for an additional 30 minutes. After 30 minutes the reaction mixture was cooled to 0° C. and then treated with 1.0 molar sodium hydroxide (4644 μL, 4.644 mmol). The reaction mixture was diluted with diethyl ether and partitioned with deionized water. The organic layer was dried with potassium carbonate 98% powder, filtered, concentrated, and dried for one minute under high vacuum to provide the title compound (170.7 mg, 0.772 mmol, 91.2% yield) as a light yellow oil.

1. temperatureto reflux
2. additiontreated with Borane-methyl sulfide complex (88.09 μL, 0.929 mmol)
3. temperatureAfter 1 hour of refluxing
4. temperatureThe reaction mixture was then heated
5. temperatureto reflux for an additional 30 minutes
6. temperatureAfter 30 minutes the reaction mixture was cooled to 0° C.
7. custompartitioned with deionized water
8. dry with materialThe organic layer was dried with potassium carbonate 98% powder
9. filtrationfiltered
10. concentrationconcentrated
11. customdried for one minute under high vacuum

ORD 기록

ord-bc8e214f41f7468e9e61f526b941a58d

출처 데이터셋

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08716498B2