Trifluoroacetic acid → HCID 178524854, compound

Methyl 2,2,2-trichloroacetimidate (0.73 g, 4.09 mmol) and trifluoroacetic acid (0.63 mL, 8.17 mmol) were added to a suspension of 4-nitrophenylenediamine (0.50 g, 3.27 mmol) in a 2:3 mixture of dichloromethane/diethyl ether (40 mL). After stirring at RT for 3 h, the reaction mixture was filtered. The residue in the filter was washed with a 1:1 mixture of dichloromethane:ether. The filtrates were combined and shaken with 1.5N aqueous sodium hydroxide (40 mL). The organic layer was removed. A 1:1 mixture of methanol/ether (40 mL) was added, and the mixture was stirred at RT overnight. The precipitated yellow solid was collected by filtration, suspended in water and the mixture acidified with 6N aqueous HCl. The precipitate was collected by filtration and dried under vacuum overnight to give the title compound (0.331 g, 49%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.56 (s, 1H), 8.20 (d, 1H), 7.79 (d, 1H). MS: m/z 208 (M+H).

1. filtrationthe reaction mixture was filtered
2. washThe residue in the filter was washed with a 1:1 mixture of dichloromethane
3. stirringshaken with 1.5N aqueous sodium hydroxide (40 mL)
4. customThe organic layer was removed
5. additionA 1:1 mixture of methanol/ether (40 mL)
6. additionwas added
7. stirringthe mixture was stirred at RT overnight
8. filtrationThe precipitated yellow solid was collected by filtration
9. filtrationThe precipitate was collected by filtration
10. customdried under vacuum overnight

ORD record

ord-5824d5ae7d7b4b99ba3d286ee96297ab

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2