Triethylamine → N-(5-Methyl-1,3,4-oxadiazol-2-yl)-N-propylcyclobutanecarboxamide

HRID 261800Notes

Reaction equation

HRID 261800 reaction equation
[CH3:1][C:2]1[O:6][C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[N:4][N:3]=1.[CH:11]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([N:7]([CH2:8][CH2:9][CH3:10])[C:15]([CH:11]2[CH2:14][CH2:13][CH2:12]2)=[O:16])=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 541521435-Methyl-N-propyl-1,3,4-oxadiazol-2-amine2×

Product 1

HCID 21315333N-(5-Methyl-1,3,4-oxadiazol-2-yl)-N-propylcyclobutanecarboxamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Methyl-2-n-propylamino 1,3,4-oxadiazole (6 g, 0.04 mol) prepared as in (b) above, was refluxed with cyclobutanecarboxylic acid chloride (5.5 g, 0.05 mol) in benzene (25 ml) in the presence of triethylamine (4.72 g, 0.05 mol) for 2 hours. The mixture was filtered and the filtrate washed with dilute HCl, saturated solution NaCHO3 and water; dried over magnesium sulphate, filtered, solvent evaporated off to yield a reddish brown liquid which was distilled twice in a vigreux flask to yield the title compound as a slightly pink liquid (b.p. 110°-111° C./0.27 mm Hg).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate washed with dilute HCl, saturated solution NaCHO3 and water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customsolvent evaporated off
  6. customto yield a reddish brown liquid which
  7. distillationwas distilled twice in a vigreux flask

Sources & evidence

ORD record
ord-1261bc12795546f5a9356a7c45b3dae1
Source dataset
uspto-grants-1979_05
Patent number
US04152442

Reaction notes

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