Cysteamine Hydrochloride → HCID 15592302, compound

HRID 1075077Notes

Reaction equation

HRID 1075077 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 15592302HCID 15592302, compoundYield 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-bbce1a95f8ca40b4a134bbc7e1a36c13
Source dataset
uspto-grants-1983_07
Patent number
US04394508

Reaction notes

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