Ethyl Acetate → 2-[{2-(1,3-Benzodioxol-5-yl)ethyl}dithio]ethyl nicotinate

HRID 1195292Notes

Reaction equation

HRID 1195292 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][S:13][CH2:14][CH2:15][OH:16])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.C(=O)([O-])[OH:27].[Na+].C(OCC)(=O)C>N1C=CC=CC=1.C1C=CC=CC=1>[C:18]([O:16][CH2:15][CH2:14][S:13][S:12][CH2:11][CH2:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)(=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 516892Sodium BicarbonateHCID 190016232-[{2-(1,3-Benzodioxol-5-yl)ethyl}dithio]ethanol

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

4 g of the 2-[{2-(1,3-benzodioxol-5-yl)ethyl}-dithio] ethanol prepared in Example 1 was dissolved in a mixture comprising 20 ml of pyridine and 50 ml of benzene to obtain a solution. 4 g of nicotinyl chloride hydrochloride was added to the solution. The obtained mixture was heated under reflux for 2 hours and poured into ice/water. The obtained mixture was weekly basified with sodium hydrogencarbonate. Ethyl acetate was added to the mixture to carry out the phase separation. The ethyl acetate layer was washed with water five times, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3:1) to obtain 5.4 g of the title compound as a colorless oil.

Workup

  1. customto obtain a solution
  2. temperatureThe obtained mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customthe phase separation
  5. washThe ethyl acetate layer was washed with water five times
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5b9626b2706446feaf0a96b8a89318e4
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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