N-Nitrosodimethylamine → HCID 15954789, compound

Temperature

-78 °C

To a stirred solution of 6.6 ml diisopropylamine in 150 dry tetrahydrofuran at 0° C. under nitrogen was slowly added 18.4 ml (2.5 m) n-butyllithium. The mixture was cooled to -78° C., and 3.2 ml N-nitrosodimethylamine was then slowly added. The latter mixture was stirred for 30 min, and 6.0 g 5-[5-(2,6-dimethyl-4-cyanophenoxy)pentyl]-3-methylisoxazole in 33 ml dry tetrahydrofuran was added dropwise. The reaction mixture was stirred at -73° C. for 8.5 hours, and 3 ml glacial acetic acid in 10 ml tetrahydrofuran was then added. The reaction mixture was stirred overnight, then concentrated, and the residue dissolved in ethyl acetate. The solution was washed with water and saturated sodium chloride, dried over magnesium sulfate and concentrated to an oily residue. The latter was chromatographed on silica gel and eluted with ethyl acetate/hexane 60:40. The product was recrystallized from ethyl acetate/hexane to give 2.69 g 4-[3,5-dimethyl-4-{[5-(3-methyl-5-isoxazolyl)pentyl]oxy}phenyl]-1-methyl-1H-1,2,3-triazole, m.p. 117-118° C.

1. customat 0° C.
2. stirringThe reaction mixture was stirred at -73° C. for 8.5 hours
3. stirringThe reaction mixture was stirred overnight
4. concentrationconcentrated
5. dissolutionthe residue dissolved in ethyl acetate
6. washThe solution was washed with water and saturated sodium chloride
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated to an oily residue
9. customThe latter was chromatographed on silica gel
10. washeluted with ethyl acetate/hexane 60:40
11. customThe product was recrystallized from ethyl acetate/hexane

ORD record

ord-662587036086486389b2c7e809b3fdde

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04857539