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

HRID 1702283Notes

Reaction equation

HRID 1702283 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].C[O-].[Na+].Cl[CH2:10][C:11]1[N:15]=[C:14]([CH3:16])[O:13][N:12]=1>CO>[CH3:16][C:14]1[O:13][N:12]=[C:11]([CH2:10][S:5][CH2:4][CH2:3][NH2:2])[N:15]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 3021573-(Chloromethyl)-5-methyl-1,2,4-oxadiazoleHCID 10942334Sodium Methoxide

Product 1

HCID 155923022-[(5-Methyl-1,2,4-oxadiazol-3-yl)methylthio]ethylamineYield 121.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Cysteamine hydrochloride (3.03 g; 26.7 mmoles) was added in several portions over a period of 10 minutes to a stirred solution of sodium methylate (2.89 g; 53.4 mmoles) in 50 ml of methanol at 0°. After stirring for 70 minutes at 0°, a solution of 3-chloromethyl-5-methyl-1,2,4-oxadiazole (3.54 g; 26.7 mmoles) in 15 ml of methanol was added dropwise over a period of 15 minutes, and the reaction mixture was allowed to stir at ambient temperature for 16 hours. The mixture was filtered, evaporated and redissolved in isopropyl alcohol, then filtered and evaporated under reduced pressure to give the title compound (5.64 g) as a yellow oil. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances δ: 3.77 (s, 2H); 2.77 (m, 4H); 2.63 (s, 3H).

Workup

  1. stirringto stir at ambient temperature for 16 hours
  2. filtrationThe mixture was filtered
  3. customevaporated
  4. dissolutionredissolved in isopropyl alcohol
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-489295e8c8614d408e207b62f1ebe625
Source dataset
uspto-grants-1983_04
Patent number
US04380638

Reaction notes

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