Hydrochloric Acid → 3,3'-Disulfanediylbis(N,N-dimethylpropan-1-amine)

In a 300 ml round-bottom flask were charged 31.6 g of N,N-dimethyl-3-chloropropylamine hydrochloride, 34.8 g of sodium thiosulfate and 100 ml of distilled water. The mixture was heated under reflux and stirred for 2 hours and then continuously heated under reflux for further 1 hour after the addition of 22.3 g of 36% hydrochloric acid. Under cooling in an ice bath, 25.3 g of 95% sodium hydroxide was slowly added to adjust pH to the alkaline range, and the mixture was subjected to extraction three times with 30 ml of tetrahydrofuran. Most of the water was removed with potassium hydroxide pellets. The extract was further dehydrated with anhydrous potassium carbonate, and the solvent was removed by distillation and distilled under reduced pressure to give a transparent colorless bis(N,N-dimethyl-3-aminopropyl)disulfide as the precursor of the mercaptoalkylamine desired in an amount of 22.5 g.

1. temperatureThe mixture was heated
2. temperatureunder reflux
3. temperaturecontinuously heated
4. temperatureunder reflux for further 1 hour
5. temperatureUnder cooling in an ice bath
6. extractionthe mixture was subjected to extraction three times with 30 ml of tetrahydrofuran
7. customMost of the water was removed with potassium hydroxide pellets
8. customthe solvent was removed by distillation
9. distillationdistilled under reduced pressure

ORD record

ord-99e3238c6ed94d5aade82836497a48aa

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05589517