HCID 86734544, compound → HCID 21448246, compound

3-(β-trans-p-chlorostyryl)-1,2,4-oxadiazole p-Chlorocinnamamidoxime (4.0 g.) was refluxed in triethylorthoformate (40 ml.) containing two drops of boron trifluoride etherate for 15 min. Thin layer chromatography after 5 mins. showed the reaction to be complete. The reaction mixture was evaporated in vacuo to a yellow solid which was dissolved in chloroform (100 ml.) and washed consecutively with 2N-hydrochloric acid (100 ml.), saturated sodium bicarbonate solution (100 ml.) and water (100 ml.). The chloroform solution was evaporated to dryness in vacuo and the yellow crystalline residue was recrystallised frm methanol to yield yellow crystalline platelets of 3-(β-trans-p-chlorostyryl)-1,2,4-oxadiazole, 3.33 g. (79%), m.p. 134°, λmax. (EtoH) 220-221, 280 nm., ε 14600, 30500, τ(CDCl3) 1,32 (1H), 2.58 (aromatic singlet), 2.30 (doublet, J=16 c./sec.), 2.92 (doublet, J=16 c./sec.) (Found: C, 57.9; H, 3.8; N, 13.3; Cl, 17.3. C10H7ClN2O requires C, 58.1; H, 3.4; N, 13.6; Cl, 17.2%).

1. customthe reaction
2. customThe reaction mixture was evaporated in vacuo to a yellow solid which
3. dissolutionwas dissolved in chloroform (100 ml.)
4. washwashed consecutively with 2N-hydrochloric acid (100 ml.), saturated sodium bicarbonate solution (100 ml.) and water (100 ml.)
5. customThe chloroform solution was evaporated to dryness in vacuo
6. customthe yellow crystalline residue was recrystallised frm methanol

ORD record

ord-8cbf9a8b31ec418aba0994e81e0621da

Source dataset

uspto-grants-1977_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04012377