Hydrazine hydrate (1:1) → 2-(3-Aminopropyl)thiooxazole

HRID 2397750Notes

Reaction equation

HRID 2397750 reaction equation
O.NN.C1(=O)[N:8]([CH2:9][CH2:10][CH2:11][S:12][C:13]2[O:14][CH:15]=[CH:16][N:17]=2)C(=O)C2=CC=CC=C12>C(O)C>[NH2:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[O:14][CH:15]=[CH:16][N:17]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 129234152-(3-Phthalimidopropylthio)oxazole

Product 1

HCID 205501192-(3-Aminopropyl)thiooxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (5.3 g.) was added carefully to a solution of 2-(3-phthalimidopropylthio)oxazole (10 g.) in ethanol (173 ml.) with stirring. The solution was then heated under reflux for 25 minutes. After cooling, and filtration from phthalhydrazide, the filtrate was concentrated under reduced pressure and the residue was re-evaporated with ethanol to yield crude 2-(3-aminopropylthio)oxazole which was washed twice with ether and dissolved in ethanol (60 ml.). Methyl isothiocyanate (2.54 g.) was added and the solution was heated under reflux for 30 minutes. Following cooling and filtration from insoluble material, the filtrate was concentrated to an oil which was chromatographed on a column of silica gel with ethyl acetate as eluant. The product obtained crystallised from ethanol-ether-n-hexane to give N-methyl-N'-[3-(2-oxazolyl)thiopropyl]thiourea (2.4 g.) m.p. 43°-45°.

Workup

  1. temperatureThe solution was then heated
  2. temperatureunder reflux for 25 minutes
  3. temperatureAfter cooling
  4. filtrationfiltration from phthalhydrazide
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was re-evaporated with ethanol

Sources & evidence

ORD record
ord-c92d311a9fec44818f56dea8926ef240
Source dataset
uspto-grants-1977_05
Patent number
US04022797

Reaction notes

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