Sulfuric Acid → HCID 86732242, compound

To a cooled (ice bath) solution of (4S,6S)-4-(2,3-difluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (4.94 g, 16.79 mmol) in sulfuric acid (20 ml, 375 mmol) was added sodium nitrate (1.855 g, 21.83 mmol) in one portion. After stirring for 15 min, ice bath was removed, and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into ice water containing potassium carbonate (18g). The resulting suspension was extracted with EtOAc (2×). The organic extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and purified by silica gel column (10-60% EtOAc/hexane) to afford (4S,6S)-4-(2,3-difluoro-5-nitrophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (5.6 g, 16.51 mmol, 98% yield) as light yellow solid in 91% pure. MS m/z=340.1 [M+H]+. Calculated for C12H10F5N3O3: 339.2

1. customice bath was removed
2. stirringthe mixture was stirred at room temperature for 1 h
3. additionThe reaction mixture was poured into ice water
4. additioncontaining potassium carbonate (18g)
5. extractionThe resulting suspension was extracted with EtOAc (2×)
6. washThe organic extracts were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated
10. custompurified by silica gel column (10-60% EtOAc/hexane)

ORD record

ord-28978ae1a9644ecf8eb629db95c90151

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296734B2