* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described.1,2 Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5°C.
With potassium carbonate In acetonitrile at 20℃; for 8h;
Synthesis of 2-[(3-bromopropyl)thio]-5-phenyl-1,3,4-oxadiazole (7a)
General procedure: A mixture of 5-phenyl-1,3,4-oxadiazole-2-thiol (6a) (534 mg, 3 mmol) and 1,3-dibromoprop- ane (600 mg, 3 mmol) were dissolved in CH3CN (10 mL). Then K2CO3 (1.38 g, 10 mmol) was added. The reaction mixture was stirred at room temperature for 8 h. Then the reaction mixture was filtered and extracted with DCM. The organic layers were washed with water and dried over anhydrous NaSO4, filtered, and concentrated in vacuum. The residue was purified by silica gel column chromatography (DCM/MeOH, 30:1 v/v) to afford 1e (538 mg, 60%) as a colorless gum.
2-bromo-1-[3-(tert-butyl)-4-methoxy-5-(morpholin-4-yl)phenyl]ethanone[ No CAS ]
[ 203268-77-3 ]
C26H28N4O5S[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate In ethanol
1.1 A, IV-1 synthesis of
2 . 03g (10mmol) compound II-1,3.70g (10mmol) compound III and 4.15g (30mmol) solid potassium carbonate in 20 ml ethanol and stirring overnight. Pouring the reaction mixture into 200 ml ice water, stirring, concentrated hydrochloric acid for adjusting pH=4,50 ml × 3 of dichloromethane extraction, combined with the phase, salt water washing, dry anhydrous sodium sulfate, the solvent evaporate the evaporimeter, the obtained residue is purified by column chromatography, get the pure product IV-1, white solid, MS, m/z=515 ([M+Na] +).
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