抄録
4-Methylaminoantipyrine (II) and 4-ethylaminoantipyrine (III), obtained from 4-formylaminoantipyrine and diethyl sulfate, were reacted with α-bromopropionic acid, and the 4-α-bromopropionylalkylaminoantipyrines (VI and VII) thereby obtained were reacted with dialkylamines, or (II) or (III) was condensed with dialkylamines, and the corresponding 4-α-dialkylaminopropionylalkylaminoantipyrines (VIII-X) were obtained. By treating 4-aminoantipyrine (I) or (II) with chloroacetamide or by treating (I) with paraformaldehyde and potassium cyanaide in dilute hydrochloric acid, (4-antipyrine)amino- (IV) and (4-antipyrine)methylaminoacetamide (V) were obtained. Reaction of (IV) and α-bromobutyryl bromide afforded N-α-bromobutyryl-(4-antipyrine)aminoacetamide (XI), which was derived to N-α-dimethylaminobutyryl-(4-antipyrine)aminoacetamide (XII). The condensation of (I) with α-haloacylanilide derivatives (XIII-XVIII), obtained from aniline derivatives and α-haloacyl halides, gave α-(4-antipyrine)aminoacelamide derivatives (XIX-XXIV).
Decomposition of sulpyrine (a) with conc. hydrochloric acid yields (II) and aminopyrine (b), and that with dil. hydrochloric acid yields (II) and a substance (c) of mp. 175°. Hydrolysis of (c) with hydrochloric acid affords (II) and formaldehyde, and its reaction with sodium hydrogen sulfite gives (a) and (II), with formic acid, (b) and 4-formylaminoantipyrine, and with benzenesulfonyl chloride, (N-methyl-N-4-antipyrinyl)benzenesulfonamide. (c) corresponds to molecular weight of 375 and was assumed to be bis (4-methylaminoantipyrinyl) methane from its ultraviolet absop-tion spectrum. Aminopyrine (b) was also obtained by the reaction of (I) and formaldehyde or formaldehyde and sodium hydrogen sulfite in hydrochloric acid.
