AMINOMALONONITRILE P-TOLUENESULFONATE synthesis

Yield:-

Reaction Conditions:

with sulfuric acid;toluene-4-sulfonic acid;acetic acid;sodium nitrite;Pt/C in water;toluene

Steps:

1 Production of aminomalonic acid dinitrile p-toluene-sulfonate
Example 1 Production of aminomalonic acid dinitrile p-toluene-sulfonate 13.8 g (0.200 mole) of sodium nitrite in 40 g of water was added to 13.2 g (0.200 mole) of malonic acid dinitrile (MDN) in 60 g of water in 30 minutes at 20° C. In this case, the pH of the solution was kept constant at 4 by the addition of sulfuric acid. The solution was stirred for 4 hours at 20° C., mixed with 70 g of 20 percent sulfuric acid and extracted with 4*90 g of ethyl acetate. The organic phase was dried for 2 hours on sodium sulfate and concentrated to 150 g. This phase containing the hydroximinomalonic acid dinitrile was mixed with 250 g of acetic acid and hydrogenated at 10 bars of hydrogen pressure and room temperature on 3.0 g of Pt/C (5 percent). The reaction mixture was filtered. The filtrate was mixed with 38.0 g (0.200 mole) of p-toluenesulfonic acid, concentrated to a total of 280 g, mixed with 600 g of toluene and allowed to stand for 12 hours at 4° C. The precipitated aminomalonic acid dinitrile p-toluenesulfonate was filtered off, washed with toluene and dried. The yield of the product was 44.93 g (74.9 percent of theory). The melting point of the product was 163.5° to 163.8° C. After recrystallization from ethanol, a product with a melting point of 167.0° to 168.0° C. was obtained.

References:

Lonza Ltd. US4827015, 1989, A

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