Cysteamine Hydrochloride → HCID 15592303, compound

HRID 1075079Notes

Reaction equation

HRID 1075079 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].C[O-].[Na+].[CH3:9][C:10]1[O:11][C:12]([CH2:15]Cl)=[N:13][N:14]=1>CO>[CH3:9][C:10]1[O:11][C:12]([CH2:15][S:5][CH2:4][CH2:3][NH2:2])=[N:13][N:14]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazoleHCID 10942334Sodium Methoxide

Product 1

HCID 15592303HCID 15592303, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Cysteamine hydrochloride (1.13 g; 0.01 mole) was added to a stirred solution of sodium methylate (1.08 g; 0.02 mole) in 20 ml of methanol at 0° under an argon atmosphere. The mixture was stirred for 1 hour at 0° and the resultant suspension was added dropwise over a period of 25 minutes to a stirred solution of 2-methyl-5-chloromethyl-1,3,4-oxadiazole (1.32 g; 0.01 mole) [prepared by the procedure described in Hel. Chim. Acta, 55, 1979 (1972)] in 15 ml of methanol at 0°. The reaction mixture was stirred at ambient temperature for 45 minutes, concentrated to near dryness, and then diluted with methylene chloride, filtered and evaporated under reduced pressure to give the title compound (1.92 g) as a yellow oil. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances δ: 3.87 (s, 2H); 2.8 (m, 4H); 2.53 (s, 3H).

Workup

  1. customprepared by the procedure
  2. customat 0°
  3. stirringThe reaction mixture was stirred at ambient temperature for 45 minutes
  4. concentrationconcentrated
  5. additiondiluted with methylene chloride
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-69137a7fe1414c8aad578ea3da28e5e9
Source dataset
uspto-grants-1983_07
Patent number
US04394508

Reaction notes

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