Ethanol → 3-[(2-Furanylmethyl)thio]propanoic acid, hydrazide

HRID 1900573Notes

Reaction equation

HRID 1900573 reaction equation
O1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:7][CH2:8][C:9]([O:11]CC)=O.[OH2:14].[NH2:15][NH2:16].[CH3:17]CO>>[O:14]1[CH:17]=[CH:5][CH:4]=[C:3]1[CH2:2][S:6][CH2:7][CH2:8][C:9]([NH:15][NH2:16])=[O:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 15141358Ethyl 3-(furylthio)propanoate

Product 1

HCID 635800953-[(2-Furanylmethyl)thio]propanoic acid, hydrazide

Procedure

To a stirring 10 mL EtOH solution of 4.29 g (20 mmol) of ethyl 3-(furylthio)propanoate was added 0.71 g (22 mmol) of hydrazine hydrate. After heating at reflux for 24 hours, the reaction was stirred for 24 hours at room temperature. The solvent was then removed under vacuum, and the residue was dissolved in EtOH and filtered through a bed of charcoal. 2.77 g (69%) of product, which was a water white viscous liquid, was recovered and was employed immediately in the manner described in Example 13, below.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 24 hours
  3. customThe solvent was then removed under vacuum
  4. dissolutionthe residue was dissolved in EtOH
  5. filtrationfiltered through a bed of charcoal
  6. customwas recovered

Sources & evidence

ORD record
ord-c4eccabbf7504456ae68d9df8b65f1d4
Source dataset
uspto-grants-1996_11
Patent number
US05576315

Reaction notes

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