Biguanide plus Biuret

Reading Inorg. Syn. Journal i've found interesting and simple synth of biguanide by melting dicyandiamide and ammonium chloride at 160-165C. So i wonder if one can condense biguanide with biuret, will it result in formation of 2,4,6,8-tetrazacyclooctane-1,3,5,7-tetramine? On scheme it looks good... Biurete can be simply made by melting of urea and keeping temp about 160C until melt solidifies.

Will it work? At least is there any worth to try this? And if yes, whitch reaction conditions will be needed, and how to not allow polymerisation to start?

Scheme:



[Edited on 14-7-2008 by Engager]

biguanide / biguanidine

I am still trying to sort this out

The difference apears to be an extra amino....
and reactions potentially producing each are similar,
perhaps allowing for each product simultaneously.

Anyway, here's a couple of patents of possible interest.

Attachment: US1409963 Biguanide Nitrate from 140C melt NH4NO3 plus Dicyanamide.pdf (177kB)
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biguanide diperchlorate PETN substitute

There's probably an easier way.

Like heating guanidine chloride at 180-185C converts
it to biguanide bichloride ( I think )

and then mix warm saturated aqueous solution
of that with ammonium perchlorate, for a double decomposition, thereby precipitating (hopefully) the
desired bangmaker

Interesting old text here....
http://books.google.com/books?id=eDs3AAAAMAAJ&pg=PA414&a...

[Edited on 17-7-2008 by Rosco Bodine]

Quote:

Originally posted by Rosco Bodine There's probably an easier way. Like heating guanidine chloride at 180-185C converts it to biguanide bichloride ( I think )

Quote:

and then mix warm saturated aqueous solution of that with ammonium perchlorate, for a double decomposition, thereby precipitating (hopefully) the desired bangmaker

Yes actualy you are missing something, biguanide and biguanidine are entirely different compounds, i attached picture to show you a difference.

Preparation of biguanide sulphate. 25.2g of dicyandiamide and 40.1g of ammonium chloride are ground to the fine state and intimately mixed. Mixture is placed to oil or parafin bath heated to 160C-165C, and held at this temperature until liquid melt is obtained (1-1.5 hour). Note: Higher temps cause mixture to melt way faster but result in formation of guanidine instead of biguanide, biguanide present only in trace ammounts in this case, so tempereture interval of 160-165 makes synth relatevely slow but is essential to formation of biguanide. After liquid melt is obtained mixture is held in bath for more 10-15 minutes, and then cooled to room temperature. Solid is crushed to small lumps and dissolved in 150 ml of hot water (90-100C), and solution is filtered to remove insoluble product - ameline. The filtrate is next treated with a slight excess of ammoniacal copper (II) sulfate solution (the excess is noted by the appearance of a slight purple coloration). The precipitated rose-red copper biguanide sulfate is filtered, washed with water, and dissolved in 35 ml. of hot 10% sulfuric acid (the temperature should not exceed 90°). The resulting solution is then cooled by immersion in an ice bath. The crude crystals which form are separated and dissolved in 25 ml. of boiling water and the solution is cooled in ice. Again the crystals which form are dissolved in 25 ml. of boiling water and the solution is cooled in ice. The resulting colorless crystals of biguanide sulfate 2-hydrate are filtered, washed first with 10 ml. of cold water and then with 10 ml. of absolute ethanol, and dried at 110° for about 15 hours. The yield of anhydrous biguanide sulfate is 9.2 g. (15.4%); m.p. 231 to 232°.



[Edited on 17-7-2008 by Engager]