Sodium → 1-[4-(3-Amino-1,2,4-oxadiazol-5-yl)phenyl]ethylamine

HRID 21781

Reaction equation

HRID 21781 reaction equation
[Na].[OH:2][NH:3][C:4]([NH2:6])=[NH:5].[C:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([NH2:18])[CH3:17])=[CH:12][CH:11]=1)(O)=O>C(O)C>[NH2:5][C:4]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]([NH2:18])[CH3:17])=[CH:12][CH:11]=2)[O:2][N:3]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 125682714-(1-Aminoethyl)benzoic acidHCID 178513189HCID 178513189, compound

Product 1

HCID 199334461-[4-(3-Amino-1,2,4-oxadiazol-5-yl)phenyl]ethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.8 g of sodium is dissolved in 60 ml of absolute ethanol, and 12 g of molecular sieve (4 Å) and 2.63 g of N-hydroxyguanidine are added. The batch is stirred for 1 hour at room temperature and then 1.14 g of 1-(4-carboxyphenyl)ethylamine are added. The resulting turbid yellowish solution is heated under reflux for 2 hours after which time it can be established by thin layer chromatography that the reaction is complete. The batch is filtered and the solvent is removed under reduced pressure. The residue is digested in water and cooled in an ice bath, and then the precipitate is isolated by filtration, washed with a small amount of water and dried under reduced pressure to give 1-[4-(3-amino-1,2,4-oxadiazol-5-yl)phenyl]ethylamine having a melting point of 150°-151°.

Workup

  1. temperatureThe resulting turbid yellowish solution is heated
  2. temperatureunder reflux for 2 hours after which time it
  3. filtrationThe batch is filtered
  4. customthe solvent is removed under reduced pressure
  5. temperaturecooled in an ice bath
  6. customthe precipitate is isolated by filtration
  7. washwashed with a small amount of water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ad657c7f3ec246bd86ff28dc08542cc1
Source dataset
uspto-grants-1995_06
Patent number
US05424441

Linked notes

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