Urazine from carbohydrazide

Uranyl chloride, 5 148 Uranyl orthophosphate 4-hydrate, U02HP04-4H20, 5 150 analysis of, 5 151 Urazine (4-aminourazole), 4 29 from carbohydrazide, 4 30 from carb ohydrazide-V-carb ox-amide, 4 31 salts of, 4 31 Urazole, 5 52... 

Preparation from Carbohydrazide. One hundred seventeen grams of carbohydrazide (1.3 mols) and 108 ml. of 12 M hydrochloric acid (1.3 mols) are" mixed in a 400-ml. beaker equipped with a mechanical stirrer and a 360° thermometer. The mixture is heated slowly on a hot plate with constant stirring. At first, there is vigorous effervescence, which may cause spattering, but this gradually subsides as evaporation continues. The temperature rises to about 215° and remains there for approximately an hour. Heating is stopped when the temperature rises above 220°. The over-all time of reaction is 4 hours. To the cooled melt, 125 ml. of water is added, and the mixture is heated to effect solution of soluble by-products (principally hydrazine hydrochloride). After the solution has cooled to room temperature, the urazine is filtered and washed with water, ethanol, and ether. The yield of dry product is 55 g. (73%)- The product melts with decomposition at 271 to 272°. 

In 1959, Belgian chemists worked out another method of synthesizing amine 194 by heating phenyl hydrazinecarboxylate (59BSB432). These authors, and then Lutz (64JOC1174), finally proved that the product obtained in all cases described earlier has structure 194. The results of Guha and De (24JCS1215) were revised, since they proposed the formation of urazine 197 from carbohydrazide with urea. The product thus obtained was found to be bisurea 195. 

Twenty-six and six-tenths grams of carbohydrazide-lV-carboxamide (0.2 mol) and 16.7 ml. of 12 M hydrochloric acid (0.2 mol) are heated together in a 200-ml. beaker until the temperature of the mixture rises to 210°. This usually requires between 60 and 90 minutes. The melt is then cooled and treated with 35 ml. of water. The suspension is heated briefly to effect complete solution and is then cooled to room temperature. The crystalline urazine is filtered and washed with water, ethanol, and ether. The product weighs about 11.5 g. (50% yield) and melts with decomposition at 270 to 272°. Purification is effected by recrystallization from 0.1 M hydrochloric acid, as described above. 

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See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

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