Chlorosuccinimide → HCID 136350291, compound

To a solution of (E)-5-phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde oxime (step C, 0.360 g, 1.41 mmol) in N,N-dimethylformamide (1.0 mL) at room temperature was added N-chlorosuccinimide (0.281 g, 2.11 mmol) in one portion. The resulting green, homogeneous reaction mixture was stirred at room temperature for 30 min. An additional 220 mg of NCS was added, and the reaction mixture was stirred for an additional 30 min. The reaction mixture was diluted with ethyl acetate (35 mL), washed with a 10% aqueous solution of lithium chloride (2×), and brine. The combined aqueous layers were extracted with ethyl acetate (35 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave a pale green solid which was triturated with ether and filtered. The white solid was rinsed with ether, and the filtrate was concentrated under reduced pressure and dried under reduced pressure overnight to give a quantitative yield of N-hydroxy-5-phenyl-4-(trifluoromethyl)isoxazole-3-carbimidoyl chloride as a green solid. The compound had an HPLC ret. time=2.72 min. (condition A); LC/MS M+1=291.0. 1H NMR (400 MHz, CDCl3) δ ppm 7.51-7.58 (m, 2H), 7.58-7.64 (m, 1H), 7.70 (d, J=7.48 Hz, 2H), 8.04 (s, 1H), and 9.69 (s, 1H).

1. stirringthe reaction mixture was stirred for an additional 30 min
2. washwashed with a 10% aqueous solution of lithium chloride (2×), and brine
3. extractionThe combined aqueous layers were extracted with ethyl acetate (35 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationConcentration under reduced pressure
6. customgave a pale green solid which
7. customwas triturated with ether
8. filtrationfiltered
9. washThe white solid was rinsed with ether
10. concentrationthe filtrate was concentrated under reduced pressure
11. customdried under reduced pressure overnight

ORD record

ord-fb043773e84b4fcaa4a6a089d9cb8d85

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216972B2