Ethanethiol → HCID 13290757, compound

HRID 1671815Notes

Reaction equation

HRID 1671815 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][CH2:13][SH:14].[H-].[Na+]>C1COCC1>[Cl:11][C:4]1[N:3]=[C:2]([S:14][CH2:13][CH3:12])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 13290757HCID 13290757, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichloro-3-nitropyridine (2.24 g, 11.6, 1.0 eq.) and EtSH (0.86 mL, 11.6 mmol, 1.0 eq.) in THF (60 mL) under nitrogen at 0° C. was added NaH (95%; 0.33 g, 13.1 mmol, 1.1 eq.). After 2.25 hr, the solution was concentrated in vacuo. The residue was dissolved in EtOAc and washed with water, saturated aqueous NaHCO3, water, and brine, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography using hexanes:EtOAc (10:0.05) as eluent afforded 6-chloro-2-(ethylthio)-3-nitropyridine as a yellow solid (1.34 g, 53%).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water, saturated aqueous NaHCO3, water, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32076d54d2084ddeba24d354e05cc557
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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