Hydrochloric Acid → N,N-Tetramethylcystamine

HRID 1082323Notes

Reaction equation

HRID 1082323 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH2:6]Cl)[CH3:4].[S:8]([O-])([O-])(=O)=[S:9].[Na+].[Na+].Cl.[OH-].[Na+]>O>[CH3:2][N:3]([CH3:4])[CH2:5][CH2:6][S:9][S:8][CH2:6][CH2:5][N:3]([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 28485N,N-TetramethylcystamineYield 113.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100 ml round-bottom flask, 8.5 g of N,N-dimethyl-2-chloroethylamine hydrochloride, 8.7 g of sodium thiosulfate and 50 ml of distilled water were charged and heated under reflux for 2 hours. 36% hydrochloric acid (5.1 g) was added, and the mixture was further heated under reflux for 1 hour. With cooling the mixture on an ice bath, 5.5 g of sodium hydroxide was slowly added to make the mixture alkaline, which was then subjected to extraction twice with 50 ml of ethyl acetate. After desiccating with anhydrous potassium carbonate, the solvent was removed by distillation and distilled under reduced pressure to give 7.0 g of bis(N,N-dimethyl-2-aminoethyl)disulfide, the precursor.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux for 1 hour
  5. temperatureWith cooling the mixture on an ice bath
  6. extractionwas then subjected to extraction twice with 50 ml of ethyl acetate
  7. customthe solvent was removed by distillation
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-945e574b76964421bacc83fe9103a1d8
Source dataset
uspto-grants-1996_12
Patent number
US05589517

Reaction notes

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