Ethylorthoformate → HCID 68125156, compound

HRID 596777Notes

Reaction equation

HRID 596777 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH:6]=[CH:7][C:8](=[N:10][OH:11])[NH2:9])([O-:3])=[O:2].[CH:16]([O-])([O-])OCC>B(F)(F)F.CCOCC>[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1/[CH:6]=[CH:7]/[C:8]1[N:9]=[CH:16][O:11][N:10]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 53630039EthylorthoformateHCID 54380485HCID 54380485, compound

Product 1

HCID 68125156HCID 68125156, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

o-Nitrocinnamamidoxime (1.84 g.) was refluxed for 1 hr. in ethyl orthoformate (15 ml.) containing boron trifluoride etherate (4 drops). The mixture was refrigerated overnight and filtered to give trans-3-o-nitrostyryl-1,2,4-oxadiazole (1.24 g., 64%), m.p. 128°. Evaporation of the filtrate gave an additional 0.51 g. (26%) of the title compound. A sample recrystallised from aqueous acetone has m.p. 120°- 121°, λmax. 247 nm, ε 18900 (Found: C, 55.2; H, 3.3; N, 19.4. C10H7N3O3 requires C, 55.3; H, 3.25; N, 19.35%).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-9fcd1a00494e43fb9634125924ae9e53
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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