1- Aminoguanidine bicarbonate

Submitted by R. L. Sheinter and Fred W. Neumann. Checked by Homer Adkins and M. J. Curry. 

The solution is immediately separated from the insoluble material by filtration on a 20-cin. Buchner funnel, and the cake is sucked as dry as possible. The residue is transferred to the 3-1. beaker, triturated well with 1 1. of water, and then separated from the liquid by filtration. In the same manner, the residue 

The zinc is purified by stirring 1.2 kg. of commercial zinc dust with 3 1. of 2% hydrochloric acid for 1 minute. The acid is removed by filtration, and the zinc is washed in a 4-1. beaker with one 3-1. portion of 2% hydrochloric acid, three 3-1. portions of distilled water, two 2-1. portions of 95% ethanol, and finally with one 2-1. portion of absolute ether, the wash solutions being removed each time by filtration. Then the material is thoroughly dried and any lumps are broken up in a mortar. 

The solution becomes basic to litmus after one-half to three-fourths of the paste has been added. Lower yields are obtained if a larger excess of acetic acid is employed. 

The state of reduction can be determined by placing 3 drops of the reaction mixture in a test tube containing 5 ml. of a 10% solution of sodium hydroxide and then adding 5 ml. of a freshly prepared saturated solution of ferrous ammonium sul- 

---

The aminoguanidine bicarbonate is pure enough for most purposes. It should not be recrystallized from hot water, since decomposition will occur. 

Numerous references for the preparation of aminoguanidine bicarbonate and other salts can be found in the excellent review article, The Chemistry of Aminoguanidine and Related Substances by Lieber and Smith. More recently, it has been prepared by treating a cyanamide solution at 20-50° with hydrazine and carbon dioxide, ... 

To 68 g. (0.5 mole) of aminoguanidine bicarbonate (p. 7) in a 500-ml. round-bottomed flask is added carefully the cold dilute sulfuric acid (0.24 mole), made from 24.5 g. of concentrated acid (sp. gr. 1.84) and 50 ml. of water. After the gas evolution has subsided, the solution is heated for 1 hour on a steam bath and then evaporated to dryness under a pressure of about 15 mm. 

The reaction of aminoguanidine bicarbonate (84) with sodium nitrite in the presence of excess acetic acid produces 1,3-ditetrazolyltriazine (89), another nitrogen-rich heterocycle (C2H3N11 = 85 % N) which readily forms explosive metal salts. The reaction of aminoguanidine bicarbonate (84) with sodium nitrite in the presence of mineral acid yields guanyl azide (90), of which, the perchlorate and picrate salts are primary explosives. Guanyl azide (90) reacts with sodium hydroxide to form sodium azide, whereas reaction with weak base or acid forms 5-aminotetrazole. ... 

Since 5-Amino-tetrazole (ATZ) was not available commercially at that time, Benson (Ref 3) also reported a method for the synthesis of ATZ of 99% purity in 70-85% yield by reaction of Na nitrate aminoguanidine bicarbonate dissolved in nitric acid, followed by treatment with Na acetate. Davis (Ref 4) prepd Cal. 50 gun proplnts and determined the optimum percentage of 5 to 10% ATZ without DNEB (Dinitroethylbenzene), but coated with 5 to 0.8% DNT, gave acceptable service ballistics. 

Davis (Ref 10, p 449) describes in derail a method of ptepn starting with 35g of aminoguanidine bicarbonate, 2500ml distd w, 15.7g of glac AcOH and 27.6g of Na nitrite. 

Aminoguanidine bicarbonate, Amm acetate, Amm phosphate, Amm sulfate, apatite, asbestos, Ba sulfate, boron nitride, cerium oxide, cryolite, dicyandiamide, dimethyl oxamide, dimethyl urea, di sodium phosphate, mercurous nitrate, methylene urea,... 

Alkyl(aryl)-l,l,l-trifluoro-4-methoxyalk-3-en-2-one reacts with aminoguanidine bicarbonate, giving 6-alkyl(aryl)-2[3-alkyl(aryl)-5-trifluoro-methyl-5-hydroxy-4,5-dihydro-l/7-pyrazol-l-yl]-4-trifluoromethylpyrimidine. The latter is converted into... 

Recently Haber reported that the synthesis of panfuran can be accomplished by a different process 5-nitrofurfurylideneacetone(M) is converted to 5-nitrofurfurylidenepyruvaldehyde hydrate by oxidation with selenium dioxide. A suspension of the pyruvaldehyde hydrate(iV) and aminoguanidine bicarbonate on heating in methanol gives panfuran base (/) ... 

---