Sodium Iodide → HCID 86722015, compound

HRID 524986Notes

Reaction equation

HRID 524986 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[O:8][C:7]([CH2:12]Cl)=[N:6]2.[I-:14].[Na+].O.[Cl-].[Na+].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[O:8][C:7]([CH2:12][I:14])=[N:6]2

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 23713072Sodium chloride dihydrateHCID 86722016HCID 86722016, compound

Product 1

HCID 86722015HCID 86722015, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-chloro-2-(chloromethyl)-4H-pyrrolo[1,2-d][1,3,4]oxadiazin-4-one (2.87 g, 13.1 mmol) in 57 mL of dry acetone under inert atmosphere was added 3.93 g (26.2 mmol) of sodium iodide and this mixture was stirred at room temperature overnight. Next day, the reaction mixture was poured into a 1/1 mixture of water/brine (100 mL) and extracted with diethyl ether (2×75 mL). The organic layers were washed with water and brine, dried (MgSO4) and concentrated in vacuum to afford 3.95 g of the title compound (95% yield).

Workup

  1. extractionextracted with diethyl ether (2×75 mL)
  2. washThe organic layers were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-1f1579847150460f99e3858b731351a5
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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