Eight hundred fifty milliliters of absolute methanol (magnesium-dried) is distilled directly, through a condenser, into a
1-l. three-necked reaction flask equipped with a
sealed mechanical stirrer and an
efficient reflux condenser protected by a
drying tube. After about
300 ml. of methanol has been distilled, the drying tube is removed from the reflux condenser, and small pieces of clean
sodium are added to the stirred
methanol at such a rate that the alcohol vapors do not escape from the condenser (Note
1). When a total of
23 g. (1 g. atom) of sodium has been added, the drying tube is replaced, the distillation of
methanol is completed (Note
1), and the system is brought to a temperature of 20–25° (other temperatures are less favorable). The inlet condenser is removed,
30 g. (0.5 mole) of dry finely ground urea (Note
2) is quickly added to the reaction mixture, and the opening is then closed by attaching a
dropping funnel. When the
urea has dissolved completely, the addition of
70 g. (0.48 mole) of diethyl oxalate (Note
2) is begun (Note
3). A white precipitate forms immediately. Stirring is continued for 1 hour after the addition of the ester has been completed (Note
4).
One hundred milliliters of concentrated hydrochloric acid is added dropwise to the mixture at a rate that causes little increase in the solution temperature, stirring is continued for a few minutes, and the mixture is filtered. The residue is washed twice with a small quantity of
methanol, and the filtrate and washings are transferred to a
2-l. two-necked flask equipped with a sealed stirrer and a vacuum take-off. The alcohol is removed under the reduced pressure of a good
water aspirator (Note
5). The practically dry solid residue is washed from the evaporator with water which is used as the recrystallization solvent (Note
6). When the bulk of the solid has dissolved, the solution is cooled slightly below the boiling point,
2 g. of activated carbon is added, and the solution is filtered through a hot
Büchner funnel by use of moderate suction. The solution yields a white, crystalline precipitate of
parabanic acid upon standing in a refrigerator overnight. The yield of purified, dried product melting at
241–243° with decomposition is
39–41.5 g. (
71.5–76%).