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

HRID 1974392Notes

Reaction equation

HRID 1974392 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 eluent. 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-d91f47d9527d447793c92095a8ffdb3d
Source dataset
uspto-grants-1976_12
Patent number
US04000302

Reaction notes

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