Triethylamine → HCID 21315337, compound

HRID 236904Notes

Reaction equation

HRID 236904 reaction equation
C[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.[CH2:18](N(CC)CC)C>C1C=CC=CC=1>[CH3:18][N:4]1[N:3]=[CH:2][O:6][CH:5]1[N:7]([CH2:8][CH2:9][CH3:10])[C:15]([CH:11]1[CH2:14][CH2:13][CH2:12]1)=[O:16]

Participants

5

Reactant 3

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

Product 1

HCID 21315337HCID 21315337, compound

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 NaHCO3 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 NaHCO3 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-92f8f67134e14fb5b678adb4f10b7c87
Source dataset
uspto-grants-1979_06
Patent number
US04158659

Reaction notes

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