Methyl iodide → HCID 22130065, compound

HRID 1416029Notes

Reaction equation

HRID 1416029 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH3:13][N:14]1[C:18]([S:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)=[C:17]([CH2:28][C:29]#[N:30])[N:16]=[C:15]1[CH3:31].CN(C)P(=O)(N(C)C)N(C)C.CI>O1CCCC1.CCCCCC>[CH3:13][N:14]1[C:18]([S:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)=[C:17]([CH:28]([CH3:1])[C:29]#[N:30])[N:16]=[C:15]1[CH3:31]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 22130162HCID 22130162, compoundHCID 178418339Butyllithium

Product 1

HCID 22130065HCID 22130065, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

In dry tetrahydrofuran (5 ml)was dissolved 49 mg (0.48 mmol)of diisopropylamine, and the solution was cooled to 0° C. To this, 0.3 ml of 1.62 M hexane solution of n-butyllithium was added under a stream of nitrogen, and the mixture was stirred for 10 minutes. The mixture was cooled to -78° C., and 85 mg (0.31 mmol)of [1,2-dimethyl-5-(3,5-dimethylphenylthio)imidazol-4-yl]acetonitrile (42d)was added, and the mixture was stirred for 15 minutes. Then, 86 mg (0.48 mmol)of hexamethylphosphoric triamide and 68 mg (0.48 mmol)of methyl iodide were added dropwise, and the mixture was stirred at -78° C. for 30 minutes. The reaction mixture was poured into ice-water, extracted with diethyl ether, and the extract was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography (ethyl acetate)to give 51 mg of 2-[1,2-dimethyl-5-(3,5-dimethylphenylthio)-1H-imidazol-4-yl]propiononitrile (43a)as oil (yield 57%).

Workup

  1. temperatureThe mixture was cooled to -78° C.
  2. stirringthe mixture was stirred for 15 minutes
  3. stirringthe mixture was stirred at -78° C. for 30 minutes
  4. extractionextracted with diethyl ether
  5. washthe extract was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (ethyl acetate)to

Sources & evidence

ORD record
ord-560c2cd1923b4429a758d22dad450444
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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