Methyl iodide → HCID 22130065, compound

HRID 1857728Notes

Reaction equation

[CH2:1]([Li])CCC.[CH3:6][N:7]1[C:11]([S:12][C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)=[C:10]([CH2:21][C:22]#[N:23])[N:9]=[C:8]1[CH3:24].CN(C)P(=O)(N(C)C)N(C)C.CI>CCCCCC>[CH3:6][N:7]1[C:11]([S:12][C:13]2[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=2)=[C:10]([CH:21]([CH3:1])[C:22]#[N:23])[N:9]=[C:8]1[CH3:24]

Participants

Conditions

Temperature: -78 °C

Procedure

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

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

Sources & evidence

ORD record: ord-1197338c29e74fb4bb059f54fade1080
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

Loading…