3-Chloropropionic acid → HCID 17914321, compound

Temperature

0 °C

A mixture of (E)-N′-hydroxyisobutyrimidamide (510 mg, 5 mmol), 3-chloropropanoic acid (542 mg, 5 mmol) and dicyclohexylcarbodiimide (1.24 g, 6 mmol) in anhydrous dioxane (20 mL) was stirred at 0° C. for 1 h and then at room temperature for an additional 1 h. The reaction was then heated at 80° C. for an additional 18 h. The reaction was filtered and the filtrate was evaporated. The resulting residue was purified by silica chromatography (0-100% EtOAc in hexanes gradient) to give 5-(2-chloroethyl)-3-isopropyl-1,2,4-oxadiazole; 1H NMR (400 MHz, CDCl3) δ 3.85 (t, J=7.2 Hz, 2H), 3.27 (t, J=7.2 Hz, 2H), 3.03 (septet, J=7.2 Hz, 1H), 1.13 (d, J=7.2 Hz, 6H); ESMS m/z 175.1 (M+H+).

1. waitat room temperature for an additional 1 h
2. temperatureThe reaction was then heated at 80° C. for an additional 18 h
3. filtrationThe reaction was filtered
4. customthe filtrate was evaporated
5. customThe resulting residue was purified by silica chromatography (0-100% EtOAc in hexanes gradient)

ORD record

ord-abb08675b4124ba0af8e3234312489a5

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859574B2