Iodoethane → HCID 54154479, compound

HRID 432578Notes

Reaction equation

HRID 432578 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:13][CH2:12][NH:11][C:10]2=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1.[CH2:18](I)[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:13][CH2:12][N:11]([CH2:18][CH3:19])[C:10]2=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 713539632-Chloro-5-{[2-(nitromethylidene)pyrrolidin-3-yl]methyl}pyridine

Product 1

HCID 54154479HCID 54154479, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g of 3-(2-chloropyrid-5-yl-methyl)-2-nitromethylidene-pyrrolidine, 0.3 g of ethyl iodide and 0.27 g of potassium carbonate in 3 ml of dimethylformamide is stirred at room temperature for 18 hours. The reaction mixture is poured onto water and extracted with diethyl ether. The ether phase is dried over magnesium sulfate and concentrated by evaporation in vacuo. The residue is chromatographed on silica gel with ethyl acetate/hexane (2:1). The title compound having a melting point of 129-131° C. (compound 5.5) is obtained.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with diethyl ether
  3. dry with materialThe ether phase is dried over magnesium sulfate
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue is chromatographed on silica gel with ethyl acetate/hexane (2:1)
  6. customis obtained

Sources & evidence

ORD record
ord-ffaf5e0a503d41a1842705ffeb3059be
Source dataset
uspto-grants-2003_12
Patent number
US06664248B2

Reaction notes

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