3-(Chloromethyl)pyridine → 3-(3-Pyridylmethyl)2-nitromethylenethiazolidine

HRID 1252125Notes

Reaction equation

HRID 1252125 reaction equation
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].[H-].[Na+].[H][H].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Cl)[CH:15]=1>C(#N)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:9]2[CH2:8][CH2:7][S:6][C:5]2=[CH:4][N+:1]([O-:3])=[O:2])[CH:15]=1

Participants

6

Reactant 4

HCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 38355832-Nitromethylene-thiazolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 542512073-(3-Pyridylmethyl)2-nitromethylenethiazolidineYield 10.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-Nitromethylenethiazolidine (2.9 g) was suspended in dry acetonitrile (30 ml), and 60% sodium hydride (0.9 g) was added under a nitrogen stream. Then, the mixture was stirred at room temperature until the generation of hydrogen ceased. A solution of 3-picolyl chloride (3.2 g) in dry acetonitrile (5 ml) was added, and the mixture was stirred at room temperature for 3 hours. Acetonitrile was distilled off under reduced pressure. Dichloromethane was added to the residue, and the mixture was washed with water. Dichloromethane was then distilled off from the dichloromethane layer. The remaining oily product was purified by column chromatography to give the desired 3-(3-pyridylmethyl)2-nitromethylenethiazolidine (0.5 g).

Workup

  1. distillationAcetonitrile was distilled off under reduced pressure
  2. additionDichloromethane was added to the residue
  3. washthe mixture was washed with water
  4. distillationDichloromethane was then distilled off from the dichloromethane layer
  5. customThe remaining oily product was purified by column chromatography

Sources & evidence

ORD record
ord-94edcb9a7c0848bdac28e21caa26dd60
Source dataset
uspto-grants-1988_05
Patent number
US04742060

Reaction notes

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