Sodium hydride → 5-(3,5-dimethylphenylthio)-4-isopropyl-1H-imidazole

HRID 1857688Notes

Reaction equation

[CH:1]([C:4]1[N:5]=[CH:6][NH:7][C:8]=1I)([CH3:3])[CH3:2].[CH3:10][C:11]1[CH:12]=[C:13]([SH:18])[CH:14]=[C:15]([CH3:17])[CH:16]=1.[H-].[Na+]>CN(C)C=O>[CH3:10][C:11]1[CH:12]=[C:13]([S:18][C:8]2[NH:7][CH:6]=[N:5][C:4]=2[CH:1]([CH3:3])[CH3:2])[CH:14]=[C:15]([CH3:17])[CH:16]=1

Participants

Conditions

Temperature: 140 °C

Procedure

In 30 ml of dry N,N-dimethylformamide was dissolved 4.0 g (16.9 mmol) of 4-isopropyl-5-iodo-1H-imidazole (4b), followed by addition of 4.68 g (33.9 mmol) of 3,5-dimethylthiophenol and 2.1 g (52.5 mmol) of 60% sodium hydride. The mixture was heated at 140° C. for 7 hours. The N,N-dimethylformamide was there distilled off under reduced pressure and, after addition of dry ice, the residue was extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was fractionated by silica gel chromatography (3% methanol-methylene chloride). The eluted crude compound was recrystallized from ethyl acetate-diisopropyl ether to provide 2.2 g (yield 53%) of 5-(3,5-dimethylphenylthio)-4-isopropyl-1H-imidazole (X=Y=Me) (9).

Workup

distillationThe N,N-dimethylformamide was there distilled off under reduced pressure
additionafter addition of dry ice
extractionthe residue was extracted with methylene chloride
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
distillationThe solvent was then distilled off under reduced pressure
washThe eluted crude compound
customwas recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-3b70644359ae4c70b4c9b908698e1da8
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

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