The Pyrolysis of Some Imidoester Hydrochlorides

The Chemistry of Imidates.

“…For the imidate XXI, when R = CH3-, a stabilizing effect was noted as compared with R = C6H6-or C1CH2CH2-; RC(=NH2Cl)OR' XXI further, when R' = Ar, a greatly enhanced stability ensued as prolonged heating at 70°C. gave little decomposition (226). When, for XXI, R = CHC12-, CCI3-, CBr3-, N02CH2-, or CC12(N02)-, the instability of the imidate salts was such that the corresponding substituted acetamides were isolated instead of the methyl imidate salts (306).…”

“…When, for XXI, R = CHC12-, CCI3-, CBr3-, N02CH2-, or CC12(N02)-, the instability of the imidate salts was such that the corresponding substituted acetamides were isolated instead of the methyl imidate salts (306). Similarly, attempts to prepare mandelimidate hydrochlorides from secondary alcohols via the Pinner synthesis have resulted in the formation of mandelamide (329), and benzyl /3-chloropropionimidate hydrochloride decomposed spontaneously into /?-chloropropionamide within a few days at room temperature (226).…”