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ChemicalBook CAS DataBase List Entacapone
130929-57-6

Entacapone synthesis

10synthesis methods
-

Yield:130929-57-6 98%

Reaction Conditions:

Stage #1: (2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamidewith aluminum (III) chloride;triethylamine in dichloromethane at 0 - 5; for 3 - 4 h;Heating / reflux;
Stage #2: with hydrogenchloride in dichloromethane at 0 - 20; for 0.5 h;

Steps:

2 Preparation of N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-acrylamide (entacapone); (I)

A round-bottom flask under nitrogen atmosphere is loaded with N,N-diethyl-2-cyano-3-(-3-methoxy-4-hydroxy-5-nitrophenyl-)-acrylamide (134 g, 0.421 mol) dissolved in dichloromethane (0.65 l) and triethylamine (128 g, 1.26 mol). The solution is cooled to 0-5° C. and aluminium trichloride (67.4 g, 0.505 mol) is added in portions. After that, the mixture is refluxed for 3-4 hours, until completion of the conversion. The reaction mixture is cooled to 0-5° C., a 20% hydrochloric acid solution (0.5 l) is dropped in the mixture, which is left under stirring at room temperature for 30 minutes. The resulting solid is filtered, washing with water (0.1 l×3), and dried in a static dryer under reduced pressure at 50° C.; 126 g are obtained. Yield: 98%.1H-NMR (300 MHz), δ (DMS0) 7.90 (d, 1H); 7.75 (d, 1H); 7.60 (s, 1H); 3.40 (m, 4H); 1.15 (m, 6H).

References:

US2008/146829,2008,A1 Location in patent:Page/Page column 4

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