Dimethylformamide → 5-(3,5-Dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde

HRID 1857690Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[CH:13]=[N:12][C:11]=2[CH:16]([CH3:18])[CH3:17])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([Li])CCC.CCCCCC.CN(C)[CH:32]=[O:33]>O1CCCC1>[CH3:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH:32]=[O:33])=[N:12][C:11]=2[CH:16]([CH3:18])[CH3:17])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In 16 ml of dry tetrahydrofuran was dissolved 800 mg (3.1 mmol) of 5-(3,5-dimethylphenylthio)-4-isopropyl-1-methyl-1H-imidazole (X=Y=Me) (10). This solution was cooled to -78° C. and 2.2 ml of n-butyllithium-n-hexane (1.66 molar) was added dropwise under nitrogen. After 5 minutes, 680 mg (9.3 mmol) of dry N,N-dimethylformamide was added and the reaction was further conducted at the same temperature for 15 minutes. This reaction mixture was poured in ice-water and extracted with diethyl ether. 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 purified by silica gel chromatography (ethyl acetate:n-hexane=1:5) to provide 644 mg (yield 73%) of Compound I-6. mp 93 to 94° C.

Workup

waitthe reaction was further conducted at the same temperature for 15 minutes
extractionextracted with diethyl ether
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
distillationThe solvent was then distilled off under reduced pressure
customthe residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:5)

Sources & evidence

ORD record: ord-4d008722a31d4e82b207d7baed5eb753
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147097

Reaction notes

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