Triethylamine → HCID 47125109, compound

O-Cyanomethyl-4-nitrophenol (8 g) was dissolved in methanol (50 mL) and to the solution was added hydroxyamine HCl (3.4 g) and triethylamine (9.4 mL). The reaction mixture was refluxed for 4 d and the solvent was removed under reduced pressure. The residue was redissolved in THF (50 mL). To the solution was added AcCl (23 mL) and triethylamine (50 mL). The reaction mixture was stirred at rt overnight, then added water (30 mL) and NaOH (18 g). The reaction solution was refluxed overnight, then diluted with water (200 mL). The aq. solution was extracted with EtOAc (2×150 mL). After separation, the combined EtOAc layers were dried, evaporated. The residue was purified by flash column chromatography (EtOAc/hexanes=1/2, 1/1, EtOAc) and recrystallized from EtOAc and hexanes to give O-(5-methyl-1,2,4-oxadiazol-3-yl)methyl-4-nitrophenol.

1. temperatureThe reaction mixture was refluxed for 4 d
2. customthe solvent was removed under reduced pressure
3. dissolutionThe residue was redissolved in THF (50 mL)
4. additionTo the solution was added AcCl (23 mL) and triethylamine (50 mL)
5. temperatureThe reaction solution was refluxed overnight
6. additiondiluted with water (200 mL)
7. extractionThe aq. solution was extracted with EtOAc (2×150 mL)
8. customAfter separation
9. dry with materialthe combined EtOAc layers were dried
10. customevaporated
11. customThe residue was purified by flash column chromatography (EtOAc/hexanes=1/2, 1/1, EtOAc)
12. customrecrystallized from EtOAc and hexanes

ORD record

ord-82c0daf71b124537bbef29dffaa6700a

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415365B2