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

HRID 1980697Notes

Reaction equation

HRID 1980697 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-bcb4e90d11204e8fac6142a818ed4280
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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