Cysteamine Hydrochloride → 2-((2-Aminoethyl)disulfanyl)pyridine hydrochloride

HRID 1596142

Reaction equation

HRID 1596142 reaction equation
C1[CH:6]=[C:5]([S:7][S:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)N=CC=1.[ClH:15].SCC[NH2:19]>CO>[ClH:15].[N:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:8][S:7][CH2:5][CH2:6][NH2:19]

Participants

4

Reactant 2

HCID 9082Cysteamine HydrochlorideHCID 650932,2'-Dipyridyl disulfide

Product 1

HCID 139852342-((2-Aminoethyl)disulfanyl)pyridine hydrochlorideYield 84.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2,2′-dipyridyldisulfide (13.2 g) was dissolved in 100 ml of methanol. Under vigorously stirring, 3.4 g of 2-mercaptoethylamine hydrochloride in 30 ml of methanol was added dropwise thereto. The reaction mixture was stirred for 1 hour and 40 minutes and the solvent was distilled off. Ethyl acetate was added to the resulting residue for crystallization and crystals were collected by filtration. Crude crystals thus obtained were recrystallized from methanol-ether. The mother liquor was concentrated and crystallized again from ether to obtain 5.62 g of S-(2-pyridylthio)-2-mercaptoethylamine hydrochloride (hereinafter referred to as Compound (2)) (yield 84%). The chemical formula of Compound (2) is shown below.

Workup

  1. stirringThe reaction mixture was stirred for 1 hour and 40 minutes
  2. distillationthe solvent was distilled off
  3. additionEthyl acetate was added to the resulting residue for crystallization and crystals
  4. filtrationwere collected by filtration
  5. customCrude crystals thus obtained
  6. customwere recrystallized from methanol-ether
  7. concentrationThe mother liquor was concentrated
  8. customcrystallized again from ether

Sources & evidence

ORD record
ord-6fd4b448e036424e9b5fd4fe736423c6
Source dataset
uspto-grants-2001_09
Patent number
US06291198B1

Linked notes

Loading…