Sodium Iodide → 2-(3-Iodomethyl-[1,2,4]oxadiazole-5-yl)-pyridine

HRID 420434Notes

Reaction equation

HRID 420434 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[O:5][N:4]=1.[I-:14].[Na+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:14][CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[O:5][N:4]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 162282342-[3-(Chloromethyl)-1,2,4-oxadiazol-5-yl]pyridine

Product 1

HCID 666575842-(3-Iodomethyl-[1,2,4]oxadiazole-5-yl)-pyridine

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

Step-2: The 2-(3-chloromethyl-[1,2,4]-oxadiazole-5-yl)-pyridine (0.550 g, 2.8 mmol) was dissolved in acetone (20 ml). To the clear solution, sodium iodide (0.843 g, 5.62 mmol) and tetra-n-butyl-ammonium iodide (0.259 g, 0.70 mmol) were added. The reaction mixture was refluxed for 2 hr. It was quenched by addition of water (20 ml) and extracted with ethyl acetate (2×25 ml). The combined organic layer was dried over Na2SO4 and evaporated under vacuum to yield 2-(3-Iodomethyl-[1,2,4]oxadiazole-5-yl)-pyridine in 90% (0.750 g) yield. MS: m/z: 288.1 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hr
  2. customIt was quenched by addition of water (20 ml)
  3. extractionextracted with ethyl acetate (2×25 ml)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-8263a8056b784540a6997bea95c9a459
Source dataset
uspto-grants-2012_01
Patent number
US08097594B2

Reaction notes

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