Acetyl chloride → HCID 14735943, compound

HRID 967752Notes

Reaction equation

HRID 967752 reaction equation
[OH:1][NH:2][C:3](=[NH:12])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13](Cl)(=O)[CH3:14]>>[CH3:13][C:14]1[O:1][N:2]=[C:3](/[CH:4]=[CH:5]/[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:12]=1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 178510913HCID 178510913, compound

Product 1

HCID 14735943HCID 14735943, compoundYield 27%

Procedure

(2E)-N-Hydroxy-3-phenyl-2-propenimidamide (1.6 g, 10 mmol) was mixed with excess acetyl chloride (30 mL), and heated to reflux. After 1 h the solution was cooled and the excess acetyl chloride was removed in vacuo. The resultant solids were triturated in hot ethyl acetate-hexane-acetone solution, and the supernatant was removed. The remaining solids were dried under high vacuum to afford 5-methyl-3-[(E)-2-phenylethenyl]-1,2,4-oxadiazole (0.50 g, 27% yield from cinnamonitrile) as a pale yellow powder. M.p. 166–168° C. 1H NMR (DMSO-d6, 300 MHz) δ 7.59 (m, 3H), 7.42 (m, 3H), 6.58 (d, J=16 Hz, 1H), 2.17 (s, 3H).

Workup

  1. temperatureheated to reflux
  2. temperatureAfter 1 h the solution was cooled
  3. customthe excess acetyl chloride was removed in vacuo
  4. customThe resultant solids were triturated in hot ethyl acetate-hexane-acetone solution
  5. customthe supernatant was removed
  6. customThe remaining solids were dried under high vacuum

Sources & evidence

ORD record
ord-ac8bd808acd24cd4b55716e49667a450
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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