Sodium Iodide → 4-[[(6-chloropyridin-3-yl)methyl](3-iodopropyl)amino]furan-2(5H)-one

HRID 552910Notes

Reaction equation

HRID 552910 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]([CH2:12][C:13]1[CH:14]=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=1)[C:6]1[CH2:10][O:9][C:8](=[O:11])[CH:7]=1.[I-:20].[Na+]>C(#N)C>[Cl:19][C:16]1[N:15]=[CH:14][C:13]([CH2:12][N:5]([CH2:4][CH2:3][CH2:2][I:20])[C:6]2[CH2:10][O:9][C:8](=[O:11])[CH:7]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 577798054-[(3-chloropropyl)[(6-chloropyridin-3-yl)methyl]amino]furan-2(5H)-one

Product 1

HCID 577798354-[[(6-chloropyridin-3-yl)methyl](3-iodopropyl)amino]furan-2(5H)-oneYield 87.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

27.50 g (91.3 mmol) of 4-[(3-chloropropyl)[(6-chloropyridin-3-yl)methyl]amino]furan-2(5H)-one (I-2) and 51.60 g (344.2 mmol) of sodium iodide in 1.2 l of acetonitrile are heated under reflux for 4 hours. Concentration of the organic phase under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate gives 31.5 g of 4-[[(6-chloropyridin-3-yl)methyl](3-iodopropyl)amino]furan-2(5H)-one.

Workup

  1. temperatureunder reflux for 4 hours
  2. customConcentration of the organic phase under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-d00f50910e4c404995725c3b7622c361
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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