Sodium Iodide → HCID 19746019, compound

HRID 2253678Notes

Reaction equation

HRID 2253678 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[C:12](=[O:13])[N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]2=[N:5]1.[I-].[Na+].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[C:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH2:13].[ClH:1].[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)=[C:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][N:4]3[C:12](=[O:13])[N:7]4[CH2:8][CH2:9][CH2:10][CH2:11][C:6]4=[N:5]3)[CH2:27][CH2:26]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15105335HCID 15105335, compoundHCID 15105352HCID 15105352, compound

Product 1

HCID 19746019HCID 19746019, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-Chloroethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]-pyridin-3(2H)-one (2.08 g), 3.1 g of sodium iodide and 100 mλ of acetonitrile were refluxed for 30 minutes, and 3.1 g of 4-[bis(4-methoxyphenyl)methylene]piperidine and 2.8 g of potassium carbonate were added thereto, followed by refluxing for 18 hours. The insoluble material was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in 100 mλ of chloroform, and the solution was applied to a column contained with 130 g of silica gel and eluted with a 15:1 (by volume) mixture of chloroform and ethanol. The eluate was concentrated to dryness, and the resulting residue was dissolved in ethanol, of concentrated hydrochloric acid was added thereto, followed by concentration to dryness. The residue was recrystallized from a mixture of ethanol and ethyl ether to obtain 0.85 g of the entitled compound as colorless crystals.

Workup

  1. temperatureby refluxing for 18 hours
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure
  4. dissolutionThe residue was dissolved in 100 mλ of chloroform
  5. washeluted with a 15:1 (by volume) mixture of chloroform and ethanol
  6. concentrationThe eluate was concentrated to dryness
  7. dissolutionthe resulting residue was dissolved in ethanol, of concentrated hydrochloric acid
  8. additionwas added
  9. concentrationfollowed by concentration to dryness
  10. customThe residue was recrystallized from a mixture of ethanol and ethyl ether

Sources & evidence

ORD record
ord-f66feef64f954baba09cc6c3bad1bd81
Source dataset
uspto-grants-1993_08
Patent number
US05232924

Reaction notes

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