Sodium Iodide → HCID 178443937, compound

HRID 275556Notes

Reaction equation

HRID 275556 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].[CH2:5]([C:7]([CH2:35][CH3:36])([CH:9](Br)[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:6].[I-:37].[Na+]>CC(C)=O>[PH:1](=[O:2])([OH:4])[OH:3].[CH2:5]([C:7]([CH2:35][CH3:36])([CH:9]([I:37])[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:6]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 178442503HCID 178442503, compound

Product 1

HCID 178443937HCID 178443937, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of diethyl 3-bromo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 29) and sodium iodide (1.30 g) in acetone (15 ml) was allowed to stand for twenty hours at room temperature in the absence of light. It was then filtered through Hyflo Super-Cel, evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give diethyl 3-iodo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.85 g, m.p. 98°-100° C.). NMR (CDCl3): δ1.3(6H,t), 1.7-1.9(2H,m), 2.5-2.6(2H,m), 4.05(4H,m), 5.3(1H,t), 7.1(6H,m), 7.3(9H,m), 7.9(1H,s). M/S: M+ 615.

Workup

  1. waitto stand for twenty hours at room temperature in the absence of light
  2. filtrationIt was then filtered through Hyflo Super-Cel
  3. customevaporated under reduced pressure
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-825b286086e042d7a525c7642fece806
Source dataset
uspto-grants-1995_02
Patent number
US05393732

Reaction notes

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