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With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h;
A typical synthetic procedure is as follows. 1,7-dibromo perylene diimide (1, 77 mg, 0.1 mmol) was dissolved into 5 mL of dimethylformamide (DMF). To which alkyl alcohol (R-OH, 0.5 mmol) and potassium carbonate (K2CO3, 70 mg, 0.5 mmol) were added. The resulted mixture was then allowed reacted under 80C for 1-4 hours. The reaction mixture was then powered into 15 mL water and the red solid was then re-dissolved in 20 mL dichloromethane (DCM) and washed with 1N hydrochloric acid and then water each for 3 times. Then, DCM layer was dried over Na2SO4. After removal of DCM, the residue was applied to chromatography with CH2Cl2/ethyl acetate (100:0-100:2) as eluents to afford the desired products 4.
With dipotassium peroxodisulfate; iron(III) chloride hexahydrate; In water; dimethyl sulfoxide; at 100℃; for 12h;
A dried reflux tube equipped witha magnetic stir bar charged with benzothiazole derivative (0.5 mmol 1.0equiv), benzylalcohol derivative (1.5mmol 3.0equiv), FeCl3·6H2O (0.1equiv), K2S2O8 (2.0 equiv), DMSO/H2O (2:1 mL) and the reaction vessel was placedin a 100C oil bath for 12 h under air. After cooling to room temperature,the mixture was diluted with ethyl acetate and directly filtered through a padof celite and washed with water. The organic phase was dried over NaSO4and removed under reduced vacuum. The residue was purified by columnchromatography eluting with ethyl acetate and hexane to afford thedesired product.
37%
With tert.-butylhydroperoxide; copper dichloride; In water; at 80℃; for 24.5h;Inert atmosphere; Schlenk technique;
General procedure: A 25 mL reaction vessel was charged with benzothiazole 1 (1.86 mmol, 1.1 equiv), benzylic alcohol 4 (1.69 mmol), CuCl2 (0.51 mmol, 0.3 equiv), and tert-butyl hydroperoxide (4.06mmol, 2.4equiv, 70% aqueous solution) under nitrogen. The reaction mixture was stirred in an ice bath for 30 min, and then stirred at 80C for 24 h. After cooling to room temperature, the mixture was purified by column chromatography using silica gel (petroleum ether/ethyl acetate) to afford the products 3.
With tetrabutylammonium bromide; In N,N-dimethyl-formamide; at 80℃; for 1.83333h;
General procedure: A mixture of alcohol (1 mmol), 1,2-phenylenediamine or 2-aminothiophenol(1 mmol), Pd(II)Cl2-BTPMNPs (0.019 g, containing 0.09mol% Pd) and (1 mmol) tetrabutylammonium bromide (TBAB, 0.01 g)in DMF (5 mL) in a round-bottomed flask equipped with a condenser wasstirred at 80 C. The progress of the reaction was monitored by TLC(eluent: n-Hexane/EtOAc, 4: 1 for benzimidazoles and n-Hexane/EtOAc, 6: 1 for benzothiazoles). The catalyst was separated by permanentmagnet and washed with EtOAc (10 mL). The crude product waspurified by recrystallization from EtOAc or EtOH to afford the purebenzimidazole. The benzothiazoles was obtained by recrystallizationfrom n-hexane/EtOAc (10: 1).
79%
With anhydrous sodium carbonate; In neat (no solvent); at 120℃;Green chemistry;
General procedure: Typically, o-phenylenediamine (1.3 mmol) or 2-aminothiophenol (1 mmol), benzyl alcohols (1 mmol), Na2CO3 (20 mol%), and Pd-NPs/Cu2(BDC)2(DABCO) (20 mg, 0.01 mol%) were added to a round-bottom flask. The reaction mixture was heated to 120 Cand stirred at for the appropriate time in air (TLC monitoring). Ethyl acetate was added to the reaction mixture and catalyst was filtered. For the purification of impure products, chromatography on silica gel was performed (EtOAc:Hep. (1:6)). The entire products characterized by melting point, CHN, 1H-NMR and13C-NMR spectroscopy.
79%
With potassium-t-butoxide; In toluene; at 20 - 110℃; for 48h;
At room temperature, add o-aminothiophenol 1a (0.6 mmol), toluene solvent and 4-methylbenzyl alcohol 2e (0.2 mmol) to the reactor in turn, stir at room temperature to fully dissolve them, and add to Example 1 in turn The prepared HKUST-1-400 catalyst (20mg), potassium tert-butoxide (0.2mmol), after dissolving, continue the reaction and place it at 110C for 2 days. After the completion of the reaction is detected by TLC, the Cu-MOF derivative material is filtered out first The HKUST-1-400 catalyst was then subjected to column chromatography to obtain the target compound 3e with a yield of 79%.
73%
With [Pd(COD)Cl(SnCl3)]; In o-dimethylbenzene; at 140℃; for 24h;
General procedure: A mixture of aniline 1 (23.28 mg, 0.25 mmol), benzyl alcohol 2 (27 mg, 0.25 mmol), [Pd(COD)Cl(SnCl3)] (3.5 mg, 0.007 mmol) in 3mL of o-xylene was stirred at 140 C for 24h. Then, solvent was removed under reduced pressure, and the mixture was subjected to column chromatography over silica gel (100-200 mesh, eluent: petroleum ether 60-80 C/ethylacetate 20:1 v/v) to afford a corresponding product 3 as a yellow color oil in 90% (41.5 mg) isolated yield.
With oxygen; In acetonitrile; under 760.051 Torr; for 10h;Schlenk technique; Sealed tube; Irradiation; Green chemistry;
General procedure: The synthesis of 2-substituted benzothiazoles from oaminothiophenols and alcohols was performed in a sealed Schlenk tube under visible light irradiation. Typically, a mixture of oaminothiophenol(0.1 mmol) and alcohol (0.3 mmol) in acetonitrile(CH3CN, 2 mL) was saturated with O2 before the mixture wastransferred into a 10 mL tube containing 10 mg of MOFs. The suspensionwas irradiated with a 300WXe lamp equipped with a UVcutfilter to remove all irradiations with wavelengths less than420 nm and an IR-cut filter to remove all irradiations with wavelengthsgreater than 800 nm. After the reaction, the suspensionwas filtered through a porous membrane (diameter 20 μm) andthe products were analyzed by GC-MS and GC-FID (ShimadzuGC-2014) with an HP-5 capillary column. The reaction, scaled upby 10 times, was conducted under similar conditions in a homemadereactor. A mixture of o-aminothiophenol (1 mmol) and benzylalcohol (3 mmol) in CH3CN (20 ml) saturated with O2 wastransferred to the homemade reactor containing 100 mg of MIL-100(Fe). The reactor was irradiated with a 300W Xe lampequipped with both a UV-cut filter and an IR-cut filter.
1-(4-methylbenzyl)-5-chloropyridin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
With 4-Methylbenzyl bromide; at 130℃; for 12h;Green chemistry;
<strong>[4214-79-3]2-hydroxy-5-chloropyridine</strong> (0.259 g, 2 mmol), 4-methylbenzyl alcohol(2.4 mmol, 1.2 equiv.) And 4-methylbenzyl bromide (0.0559 ml, 20 molpercent)were added successively to a tubular reactor,, Sealed directly in air, and thenheated to 130 ° C for 12 h undersolvent-freeconditions.After the TLC monitoring reaction was complete, the product was purified by column chromatography and the yield was91percent.
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