Hydrochloric Acid → 5-Methyl-N-propyl-1,3,4-oxadiazol-2-amine

HRID 236903Notes

Reaction equation

HRID 236903 reaction equation
[C:1]([NH:4][NH:5][C:6]([NH:8][CH2:9][CH:10]=[CH2:11])=[O:7])(=O)[CH3:2].O=P(Cl)(Cl)Cl.Cl.[OH-].[Na+]>O>[CH3:2][C:1]1[O:7][C:6]([NH:8][CH2:9][CH2:10][CH3:11])=[N:5][N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride2×HCID 21315322HCID 21315322, compound

Product 1

HCID 541521435-Methyl-N-propyl-1,3,4-oxadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-Acetyl-4-n-propyl semicarbazide (35 g, 0.22 mol) prepared by method (a) above, was refluxed with POCl3 (150 ml) for 2 hours, until no more HCl was evolved. Excess POCl3 was taken off by a water pump and the mixture poured into 200 ml. iced water and neutralized with 50% NaOH to pH 7. Red oil was extracted with dichloromethane (2×180 ml), dried, filtered and evaporated down to yield an oil which was distilled in a vigreux flask to yield the title compound as a pink liquid which crystallised upon standing to a solid. (m.p. 46.5°-47.5° C.).

Workup

  1. additionthe mixture poured into 200 ml
  2. extractionRed oil was extracted with dichloromethane (2×180 ml)
  3. customdried
  4. filtrationfiltered
  5. customevaporated down
  6. customto yield an oil which
  7. distillationwas distilled in a vigreux flask

Sources & evidence

ORD record
ord-6de83977490b4f708a430abead3b3b53
Source dataset
uspto-grants-1979_06
Patent number
US04158659

Reaction notes

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