Cysteamine Hydrochloride → 2-Butylthiomorpholin-3-one

HRID 1608121Notes

Reaction equation

HRID 1608121 reaction equation
[OH-].[K+].Cl.[NH2:4][CH2:5][CH2:6][SH:7].Br[CH:9]([CH2:15][CH2:16][CH2:17][CH3:18])[C:10](OCC)=[O:11]>C(O)C>[CH2:15]([CH:9]1[S:7][CH2:6][CH2:5][NH:4][C:10]1=[O:11])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14797Potassium HydroxideHCID 79072Ethyl 2-bromohexanoate

Product 1

HCID 132340922-Butylthiomorpholin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide (56 g) was added to a suspension of cysteamine, hydrochloride (56.6 g) in absolute ethanol (300 ml) followed by dropwise addition of ethyl 2-bromohexanoate (111.5 g). When the exothermic reaction ceased, the mixture was refluxed for 3 hours and filtered. Concentration of the filtrate in vacuo gave the title compound as a viscous oil which was used in the next step without purification.

Workup

  1. customWhen the exothermic reaction
  2. temperaturethe mixture was refluxed for 3 hours
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b51a1ad99e9941cf8c8b120aa41b65a1
Source dataset
uspto-grants-1989_09
Patent number
US04870063

Reaction notes

Loading…