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A 2.0 M solution of dimethylamine (74.8 mL, 150 mmol) and triethylamine(37.9 mL, 272 mmol) was added to 500 mL of diethyl ether,Compound A-1 (24 g, 138 mmol) was slowly added dropwise and stirred for 30 minutes.The resulting solid was filtered, and the filtrate was distilled to obtain the compoundA-2 (19.8 g, yield 83%).
83%
With triethylamine; In diethyl ether; for 0.5h;
A 2.0 M solution of dimethylamine (74.8 mL, 150 mmol) andTriethylamine (37.9 mL, 272 mmol) was added to a solution of After adding 500 mL of diethyl ether,Compound A-1 (24 g, 138 mmol) was slowly added dropwise and stirred for 30 minutes. The resulting solid was filtered,The filtrate was distilled to obtain Compound A-2 (19.8 g, yield 83%)
With triethylamine; In diethyl ether; for 0.5h;
After adding a 2.0 M solution of dimethylamine (74.8 mL, 150 mmol) and triethylamine (37.9 mL, 272 mmol) into 500 mL of diethyl ether, Compound A-1 (24 g, 138 mmol) And stirred for 30 minutes. The resulting solid was filtered, and the filtrate was distilled to obtain the compoundA-2 (19.8 g, yield 83%) was prepared
With lithium diisobutylmorpholinoaluminum hydride; In tetrahydrofuran; hexane; at 0℃; for 0.5h;
General procedure: The following procedure for reduction of N,N-dimethylbenzamide with LDBMOA is representative. To a solution of N,N-dimethylbenzamide (0.149 g, 1.0 mmol) in THF (10.0 mL) containing naphthalene as an internal standard was added LDBMOA (2.4 mL, 0.5 M in THF-hexanes, 1.2 mmol) at 0 C. After 30 min, the reaction mixture was hydrolyzed with 1 N aq HCl (10 mL) and extracted with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate, and filtered. After the removal of solvents in vacuum and purification of residue by column chromatography on silica gel gave benzaldehyde (0.103 g, 97%).
> 99%Chromat.
With C11H25AlNO4(1-)*Na(1+); In tetrahydrofuran; toluene; at 0 - 20℃; for 0.5h;
General procedure: The following experimental procedure describes a representative example of the partial reduction of N,N-dimethylbenzamide to benzaldehyde. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum,was charged with N,N-dimethylbenzamide (0.07 mL,0.5 mmol) and THF (5 mL). After cooling to 0 C, piperidine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at room temperature. The reaction was quenched with 1 N aqueous HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The organic layer was dried over anhydrous magnesium sulfate. GC analysis showed quantitative conversion to benzaldehyde. All products listed in Table 2 were confirmed through comparison with the GC data of authentic samples.
2-methylthio-4-chloro-5-(4-chlorobenzyl)pyrrole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium acetate; trichlorophosphate; In water;
EXAMPLE 2B Preparation of 2-methylthio-4-chloro-5-(4-chlorobenzyl)pyrrole (Step 2x) In a separate reaction, <strong>[14062-80-7]N,N-dimethyl-4-chlorobenzamide</strong> (1.10 g, 6.0 mmoles) was heated in a solution of dry 1,2-dichloroethane (20 ml), containing phosphorus oxychloride (0.55 ml, 6 mmoles), for 0.5 hour. (Vilsmeier-Haack reagent). The solution containing the Vilsmeier-Haack reagent was added to the solution from Example 2A and the mixture was heated at reflux temperature in a nitrogen atmosphere for 24 hours. At this time, there was added very carefully to the cooled reaction mixture a solution of sodium acetate (2 g, 30 mmoles) in water (10 ml) and the mixture was heated at reflux temperature for a further 2 hours. T.L.C. (ethyl acetate-hexane; 1:4) showed the formation of a new spot (yellow) more polar than the starting material. The solvent was removed in vacuo, water was added to the residue, the product was extracted into ethyl acetate, the extract was dried and evaporated in vacuo.
With sodium acetate trihydrate; In 1,1-dichloroethane; water; 1,2-dichloro-ethane;
EXAMPLE I 2-p-Chlorobenzoylpyrrole A mixture of 183 g (1 mole) of p-chloro-N,N-dimethylbenzamide and 153g (1 mole) of phophorous oxychloride in 300 ml of 1,2-dichloroethane is heated under reflux for 30 minutes, after which a solution of 67g (1 mole) of pyrrole in 300 ml of dichloroethane is added drop-wise. It is cooled and a solution of 408g (3 moles) of sodium acetate trihydrate in 1600 ml of water is added dropwise for 45 minutes, after which the mixture is again heated under reflux for 30 minutes. The resulting mixture is poured onto ice, the organic layer is separated, and the aqueous layer is washed with chloroform. The combined organic solutions are washed with sodium bicarbonate and brine and dried over magnesium sulfate. Evaporation of the solvent in vacuo gives a dark oil, which is distilled in vacuo through a heated Vigreaux column to give a white solid; mp 106-9 C. It is recrystallized from cyclohexane to give 2-p-chlorobenzoylpyrrole as white needles; m.p. 110-113 C.
With di-tert-butyl peroxide; copper(II) bis(trifluoromethanesulfonate); In 1,2-dichloro-ethane; at 130℃; for 12h;Sealed tube;
General procedure: A 50 mL sealed tube (with a Teflon high pressure valve) equipped with a magnetic stir bar was charged with Cu(OTf)2 (0.05 mmol), followed by carboxylic acid (0.5 mmol), formamide (2.0 mmol), tert-butyl peroxide (DTBP, 1 mmol), and DCE (1 mL). After the reaction mixture was stirred at 130 C for 12 h, it was allowed to cool to ambient temperature. The reaction mixture was diluted with ethyl acetate, and then filtered through a small pad of Celite. The filtrate was washed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL, twice). The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel preparative TLC to give the corresponding product.
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