Potassium Iodide → N-(2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl)phthalimide

HRID 1973441

Reaction equation

HRID 1973441 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]1[CH3:12].[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K].[I-].[K+].CN(C)C=O>C1(C)C=CC=CC=1>[CH3:12][C:5]1[N:4]([CH2:3][CH2:2][N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 832101-(2-Chloroethyl)-2-methyl-5-nitroimidazoleHCID 24194345Phthalimide potassium salt

Product 1

HCID 120116N-(2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl)phthalimide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 17.0 parts of 1-(2-chloroethyl)-2-methyl-5-nitroimidazole, 18.0 parts of potassium phthalimide, and 2.0 parts of potassium iodide in 240 parts of dimethylformamide is heated in a boiling water bath for 3 hours with stirring. Stirring is then continued for 16 hours at room temperature. The resulting brown mixture is diluted with 870 parts of toluene and the toluene solution is washed with several portions of water. The toluene solution is dried over sodium sulfate and the solvent is evaporated to leave a residue which is digested with cold alcohol. The alcohol solution is then cooled and the precipitate which forms is separated by filtration and recrystallized from ethanol to give N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]phthalimide melting at about 177° C. This compound has the following formula ##STR6##

Workup

  1. temperatureis heated in a boiling water bath for 3 hours
  2. stirringStirring
  3. washthe toluene solution is washed with several portions of water
  4. dry with materialThe toluene solution is dried over sodium sulfate
  5. customthe solvent is evaporated
  6. customto leave a residue which
  7. customthe precipitate which forms is separated by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-513ccd2c1b85446794e18bd6e223f312
Source dataset
uspto-grants-1976_12
Patent number
US03997572

Linked notes

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