Cysteamine Hydrochloride → 2-[(4-Methyl-1,2,5-oxadiazol-3-yl)methylthio]ethylamine

HRID 1075074Notes

Reaction equation

HRID 1075074 reaction equation
O[CH2:2][C:3]1[C:7]([CH3:8])=[N:6][O:5][N:4]=1.Cl.[NH2:10][CH2:11][CH2:12][SH:13]>Br>[CH3:8][C:7]1[C:3]([CH2:2][S:13][CH2:12][CH2:11][NH2:10])=[N:4][O:5][N:6]=1

Participants

4

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 1896971(4-Methyl-1,2,5-oxadiazol-3-yl)methanol

Product 1

HCID 131028982-[(4-Methyl-1,2,5-oxadiazol-3-yl)methylthio]ethylamine

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 3-hydroxymethyl-4-methylfurazan (2.49 g; 21.8 mmoles) [prepared in Step A] and 2-aminoethanethiol hydrochloride (2.48 g; 21.8 mmoles) in 60 ml of 48% aqueous hydrobromic acid was stirred and heated at reflux temperature for 23 hours and then at ambient temperature for 40 hours. The excess hydrobromic acid was removed under reduced pressure, and the oil residue was dissolved in isopropyl alcohol, filtered through Celite and the product was crystallized from the filtrate. Recrystallization from isopropyl alcohol yielded the title compound as the hydrobromide salt, mp 142°-143°.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 23 hours
  3. customThe excess hydrobromic acid was removed under reduced pressure
  4. dissolutionthe oil residue was dissolved in isopropyl alcohol
  5. filtrationfiltered through Celite
  6. customthe product was crystallized from the filtrate
  7. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-fdb4cb2bde4f4b39a843095a6ad22ff6
Source dataset
uspto-grants-1983_07
Patent number
US04394508

Reaction notes

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