Sodium Iodide → HCID 20455144, compound

HRID 1902836Notes

Reaction equation

HRID 1902836 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10].[I-:12].[Na+]>CC(CC)=O>[I:12][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 3272351-(2-chloroethyl)-2-nitroimidazole

Product 1

HCID 20455144HCID 20455144, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

163.4 g of 1-(2-chloroethyl)-2-nitroimidazole and 200.4 g of sodium iodide were heated under reflux for 4.5 hours in 1 liter of ethyl methyl ketone. After cooling, the mixture was filtered, the solvent was evaporated off, the residue was partitioned between 2 liters of dichloromethane and 1 liter of water and the organic phase was washed twice with 1 liter of water each time and evaporated. Crystallization from 1 liter of isopropanol yielded 206 g of 1-(2-iodoethyl)-2-nitroimidazole, m.p. 79°-82° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe solvent was evaporated off
  4. customthe residue was partitioned between 2 liters of dichloromethane and 1 liter of water
  5. washthe organic phase was washed twice with 1 liter of water each time
  6. customevaporated
  7. customCrystallization from 1 liter of isopropanol

Sources & evidence

ORD record
ord-679a3c4291a44992ad768e1d0f20a3a2
Source dataset
uspto-grants-1982_12
Patent number
US04366166

Reaction notes

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