Amidosulfonate, potassium

Formation of the partially saturated nitro derivatives 60 and 61 was reported by a Russian team <1994KGS1129>. The two products were obtained under fairly complicated reaction conditions when aminotetrazole 42 was first treated with potassium amidosulfonate and formaldehyde at pH = 4 followed by addition of nitric acid, methylamine, and acetic anhydride, product 60 was obtained in 24% yield. The same reaction, however, carried out at pH = 6 gave rise to formation of the acetoxy compound 61 in 21% yield. 

The W-process is based on the condensation of potassium amido-sulfonate with formaldehyde, and the nitration of the condensation product as shown in Reaction 7.13 (overleaf). Potassium amidosulfon-ate and formaldehyde are reacted together to produce potassium methyleneamidosulfonate. This product is nitrated to RDX by a mixture of nitric and sulfuric acids. 

W process (inventor Wolfram) potassium amidosulfonate and formaldehyde are reacted to give potassium methyleneamidosulfonate (CH2 = N-SO3K), which is then nitrated to Cyclonite by a nitric acid-sulfuric acid mixture. 

Using a new process, ADN can be prepared in a very environmentally friendly manner (without the use of chlorinated organic solvents) by the direct nitration of salts (potassium or ammonium) of sulfamic acid (amidosulfonic acid, H2N-S03H) using mixed acid (HN03/H2S04) ... 

An alternative synthesis route for acesulfame potassium starts with the reaction between diketene and amidosulfonic acid. In the presence of dehydrating agents, and after neutralization with potassium hydroxide, acesulfame potassium is formed. 

AMMONIUM AMIDOSULFONATE (7773-06-0) A powerful oxidizer may cause fire and explosions on contact with combustibles and reducing agents. A spontaneous reaction in hot acid solutions when enclosed or on contact with hot water, potassium, sodium, sodium nitrite, metal chlorates. Corrosive to mild steel. The sulfamate will be decomposed by raising temperature to 320°F/160°C, but elevated temperature causes a highly exothermic reaction. 

From amidosulfonic acid chloride the corresponding acid fluoride (XC) may be made by reaction with potassium fluoride in boiling acetonitrile (7), or by the reaction of (LXXXVI) with NaF followed by careful hydrolysis (70). Amidosulfonic acid fluoride is colorless, melts at 8°, and is soluble... 

Potassium nitrllosulfonate (60 g.) Is boiled for 75 minutes with 300 ml. of water. The solution is then neutralized with 20 g. of K3CO3 and evaporated to dryness. The residue is extracted with 80% cohol for 46 hours in a Soxhlet apparatus. Cooling of the alcoholic solution yields 13.5 g. of amidosulfonate (67% of theoretical). 

Asymmetric phase-transfer catalytic addition of cyanide to C=N, C=0, and C=C bonds has been recently explored, which has been demonstrated to be an efficient method toward the synthesis of a series of substituted chiral nitriles. In this context, Maraoka and coworkers disclosed an enantioselective Strecker reaction of aldimines by using aqueous KCN [140]. In this system, the chiral quaternary ammonium salts (R)-36e bearing a tetranaphthyl backbone were found to be remarkably efficient catalysts (Scheme 12.25). Subsequently, this phase-transfer-catalyzed asymmetric Strecker reaction was further elaborated by use of a-amidosulfones as precursor of N-arylsulfonyl imines. Interestingly, the reaction could be conducted with a slight excess of potassium cyanide [141] or acetone cyanohydrin [40] as cyanide source, and good to high enantioselectivities were observed. In contrast, the asymmetric phase-transfer-catalytic cyanation of aldehydes led to the cyanation products with only moderate enantioselectivity [142]. 

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