2-(3-Phthalimidopropylthio)oxazole → 2-(3-Aminopropyl)thiooxazole

HRID 26875Notes

Reaction equation

HRID 26875 reaction equation
[H-].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 129234152-(3-Phthalimidopropylthio)oxazoleHCID 86602801Hydrazine monohydride

Product 1

HCID 205501192-(3-Aminopropyl)thiooxazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydride (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-oxazolylthio)propyl]thiourea (2.4 g.), m.p. 43°-45°. (Found: C, 41.7; H, 5.9; N, 18.3; S, 27.5. C8H13N3OS2 requires: C, 41.5; H, 5.7; N, 18.2; S, 27.7).

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-23b528b2952e48dd80dd02cb2f4f659c
Source dataset
uspto-grants-1979_04
Patent number
US04151288

Reaction notes

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