Hydrochloric Acid → 2-[{2-(1,3-Benzodioxol-5-yl)ethyl}dithio]ethyl nicotinate hydrochloride

HRID 486932Notes

Reaction equation

HRID 486932 reaction equation
[C:1]([O:9][CH2:10][CH2:11][S:12][S:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[ClH:25]>C(OCC)(=O)C>[ClH:25].[C:1]([O:9][CH2:10][CH2:11][S:12][S:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 190016562-[{2-(1,3-Benzodioxol-5-yl)ethyl}dithio]ethyl nicotinate

Product 1

HCID 190016842-[{2-(1,3-Benzodioxol-5-yl)ethyl}dithio]ethyl nicotinate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2.5 g of the 2-[{2-(1,3-benzodioxol-5-yl)ethyl}-dithio]ethyl nicotinate prepared in Example 3 was dissolved in 20 ml of ethyl acetate, followed by the addition of a solution of hydrochloric acid in ethyl acetate. The mixture was distilled to remove the solvent. The residue was dissolved in a methanol/ethanol mixture, followed by the filtration. The filtrate was concentrated and recrystallized from an ethanol/isopropyl ether mixture to obtain 2.5 g of the title compound as a colorless crystal.

Workup

  1. distillationThe mixture was distilled
  2. customto remove the solvent
  3. dissolutionThe residue was dissolved in a methanol/ethanol mixture
  4. filtrationfollowed by the filtration
  5. concentrationThe filtrate was concentrated
  6. customrecrystallized from an ethanol/isopropyl ether mixture

Sources & evidence

ORD record
ord-5ffd04f0653a4f3fb2dcfffefba006c9
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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