Benzylamine → HCID 10800431, compound

50 g (34.5 mL, 14.3 mmol) 3,4-difluoronitrobenzene and 44.6 mL (408.6 mmol) benzylamine were combined with 600 mL acetonitrile, and then 82.3 mL (471.5 mmol) N,N-diisopropylethylamine (DIPEA) was added thereto. The resultant mixture was slowly heated to reflux. The reaction substantially completed after refluxing 5 hours, as monitored by a real-time thin layer chromatography (TLC). Then, heating was stopped and the mixture was allowed to cool to room temperature, resulting in the precipitation of a colorless transparent crystal. The mixture was filtered when substantially no more crystal precipitated. The filtrate was evaporated in a rotatory evaporator to afford a yellowish solid, which was recrystallized with ethanol to obtain a yellow crystal. Then, the yellow crystal was dried and weighed 72.5 g, with a yield of 93.7%.

1. customThe reaction
2. temperatureafter refluxing 5 hours
3. temperatureThen, heating
4. customresulting in the precipitation of a colorless transparent crystal
5. filtrationThe mixture was filtered when substantially no more crystal
6. customprecipitated
7. customThe filtrate was evaporated in a rotatory evaporator
8. customto afford a yellowish solid, which
9. customwas recrystallized with ethanol
10. customto obtain a yellow crystal
11. customThen, the yellow crystal was dried

ORD record

ord-eaf682eefc014786be63240e31d44783

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946436B2