Water → HCID 68124900, compound

HRID 596776Notes

Reaction equation

HRID 596776 reaction equation
[CH:1](/[C:9]1[N:13]=[CH:12][O:11][N:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O>C(O)C.[Hg]>[CH:1](/[C:9]1[N:13]=[CH:12][O:11][N:10]=1)=[CH:2]/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 64414463-[(E)-2-Phenylethen-1-yl]-1,2,4-oxadiazole

Product 1

HCID 68124900HCID 68124900, compound

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 702EthanolSolvent

Procedure

3-(trans-Styryl)-1,2,4-oxadiazole (0.75 g.) in absolute ethanol (750 ml.) was irradiated at room temperature, under nitrogen for a total of 31 hr. using a medium pressure mercury vapour arc tube contained in a water cooled glass well immersed in the solution. The ultraviolet spectra of suitably diluted aliquots showed a reduction in the intensity of absorption at ca. 274 nm over the period of irradiation. The colourless solution was evaporated to a low volume when the trans isomer (0.11 g.), m.p. 84° , λmax. (EtOH) 274 nm (ε 26,200) separated. Evaporation of the mother liquors to dryness gave a solid and an oil. The oil was separated and thoroughly dried to give 3-(cis-styryl)-1,2,4-oxadiazole contaminated with ca. 25% by weight of the trans-isomer, λmax. (EtOH) 272-273 nm (ε 14,300), pmr. shows cis-protons at 2.92 and 3.50 (J = 12.5) and confirms the presence of the transisomer.

Workup

  1. customin the intensity of absorption at ca. 274 nm
  2. customover the period of irradiation
  3. customThe colourless solution was evaporated to a low volume when the trans isomer (0.11 g.), m.p. 84° , λmax
  4. custom(EtOH) 274 nm (ε 26,200) separated
  5. customEvaporation of the mother liquors to dryness
  6. customgave a solid
  7. customThe oil was separated
  8. customthoroughly dried

Sources & evidence

ORD record
ord-43af3e5173a24e8bb83a34ed8d864bed
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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