Formaldehyde bisulfite addition compound from

Aminoimidazo[l,2-a]pyrazine (456) has been prepared by the reaction of 2-aminopyrazine (455) with sodium cyanide and the bisulfite addition compound from formaldehyde (68TL3873). Another 3-aminoimidazo[l,2-a]pyrazine (458) was made by the reaction of the tetrahydropyrazine (457) with a-amino-a-cyanoacetamide (67MI41000, 67MIP41000). 

The yields of nitro alcohols from simple nitroparaffins and aliphatic aldehydes or benzaldehyde are usually above 60%. The condensations are generally carried out with aqueous ethanolic sodium hydroxide, although weaker bases are sometimes desirable to prevent polymerization of the aldehyde. Sodium bisulfite addition compounds of the aldehydes are sometimes used. Better results are obtained with sodium methoxide than with alkali hydroxides in the condensation of nitroethane with formaldehyde. Sodium alkoxides are also used to effect the condensation of nitroethane with acetone and cyclohexanone. Condensation proceeds to the nitroalkanediol stage in certain cases with both nitromethane and with formaldehyde. ... 

Ingles heated a solution of n-glucose, sodium sulfite, and bisulfite, removed the cations, and steam-distilled the residue. The product, free of carbonyl-bisulfite addition compounds, was chromatographed on an ion-exchange resin, giving a sulfonic acid. This acid yields a crystalline brucine salt and phenyl- and (2,4-dinitrophenyl)-osazones. The osazones consume 1 mole of periodate per mole, liberating 1 mole of formaldehyde but no formic acid. The (2,4-dinitrophenyl)osazone also forms a diacetate. The acid is oxidized by sodium hypoiodite, taking up 1 mole of oxidant per mole. From these reactions and the possible reaction mechanisms for its formation, structure (41), a 3,4-dideoxy-4-sulfo-n-hexosulose, was proposed for the sulfonic acid. ... 

Stelling (1928) found an absorption band in formaldehyde and acetone bisulfite addition compounds at 4992.0 A similar to that in sulfonic acids at 4992.2 and differing from that of metal alkyl (4996.0) and dialkyl sulfites (4997.7). He concluded from this that the sulfonic acid structure must be present. Raman spectral examinations of several aldehyde and ketone bisulfites by Caughlan and Tartar (1941) revealed the presence of a carbon-sulfur bond, possibly a carbon-hydroxyl bond, but no carbon doubly bonded to oxygen. This thus aided in discrediting both the tripartite molecule and the sulfurous acid ester structures. Sundman (1949) believes that formation of a stable monomolecular complex of boric acid and glucose bisulfite would be impossible if Schroeter s tripartite molecular structure were correct. His examinations of this complex led him to believe that its structure could be represented only by ... 

On reaction of formaldehyde solution, sodium bisulfite, and ammonia at 1Q-7TYC an arnino derivative of the aldehyde bisulfite compound is produced. On cooling and acidifying, the parent acid crystallizes from the reaction mixture b Backer and Mulder haA e showm that this product is aminomethanesulfonic acid (NHaCHjSOgH) and not a sulfurous ester, as was fiii st supposed. This evidence ser es as an additional check on the bisulfite compound structure. The formation of sodium aminomethane sulfonate is indicated in the following equation ... 

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