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Synthesis of Pyrazolo Heteroaromatic Compounds by Means of 5-Amino-3-methyl-1-phenylpyrazole-4-carbaldehyde

✍ Scribed by Dipl.-Chem. Jochen Häufel; Prof. Dr. Eberhard Breitmaier


Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
128 KB
Volume
13
Category
Article
ISSN
0044-8249

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✦ Synopsis


composition, and IR spectrumi3] with the product prepared from SOClz and HzS,. This new, more productive synthetic route requires much less time and experimental effort than the former preparation.

Procedtwe:

Sg (3.76g, 14.7mmol)isdissolved in CHzC12 (800ml) by refluxing. The homogeneous solution is slowly cooled to 0°C and protected from light by a black cloth. A freshly prepared solution of trifluoroperacetic acid [obtained by suspension of 50% H r 0 2 ( l g , 14.7mmol) in CH2C12 (50ml) at 0°C and rapid addition of trifluoroacetic anhydride ( 5 ml, 36mniol)l is added dropwise over 1 h to the stirred reaction mixture, which assumes an intense yellow hue. Concentration in a vacuum at 20°C bath temperature to 1/3 of the original volume leads to precipitation. Further crystallization is induced by cooling to -20°C. The precipitate is collected on a glass frit, washed with CHzC12, and dried in a vacuum. The procedure yields 1.8g of almost pure S 8 0 which can be isolated analytically pure by recrystallization from CS2.


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