The Characteristics of Formamidine acetate

In a 500-ml. three-necked alembic able with a abatement condenser, a gas-inlet tube (Note 1) extensive to the basal of the flask, a thermometer, and a alluring stirrer is placed a admixture of 90.0 g. of triethyl orthoformate (Note 2) and 49.2 g. of arctic acerb acid. The alembic is absorbed in an oil ablution maintained at 125–130° (Note 3). When the centralized temperature of the admixture alcove 115°, a abstinent beck of ammonia is introduced. As the temperature decreases gradually, active refluxing is empiric (Note 4). Formamidine acetate starts to accumulate from the baking admixture afterwards 20–30 minutes. The ammonia breeze is connected until no added abatement in temperature is empiric (Note 5). The admixture is cooled to allowance temperature, the accelerate calm by filtration and done thoroughly with 50 ml. of complete ethanol. The crop of achromatic formamidine acetate is 53.0–55.8 g. (83.8–88.2%), m.p. 162–164° (Note 6). Evaporation of the mother liquor beneath bargain burden followed by air-conditioned gives a baby added bulk of artefact (1.0–2.2 g.) (Note 7).
Because formamidine hydrochloride is acutely deliquescent, ample affliction have to be acclimatized in its alertness if satisfactory after-effects are to be achieved. Furthermore, formamidine hydrochloride cannot be acclimated anon in a lot of abstract reactions; it have to be advised aboriginal with a birthmark of abject to deliver chargeless formamidine. The aforementioned brake applies to the methosulfate alkali of formamidine; in addition, complications in amalgam may be advancing in this closing case because methyl hydrogen sulfate itself is an able methylating agent.6
By contrast, formamidine acetate is not hygroscopic and no accurate affliction charge be taken to assure it from atmospheric moisture. Furthermore, formamidine acetate can be acclimated anon after above-mentioned analysis with abject in syntheses acute chargeless formamidine.2,7,8,9,10 Finally, this alertness of formamidine is by far the simplest and a lot of acceptable yet reported; it obviates the call of application either baneful (hydrogen cyanide) or bulky (Raney nickel) reagents, and the adjustment can be acclimatized to the alertness of N,N'-disubstituted formamidines by barter of primary amines for ammonia.
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