Recherches sur la formation et la transformation des esters LXXXI [1]. Sur la réaction d'isothiocyanates avec l'acide hydrazinoéthylphosphorique, et de l'isocyanate de phényle avec l'acide colaminephosphoreux

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Abstract
Hydrazinoethyl phosphoric monoester has been prepared by reacting hydrazinoethanol with polyphosphoric acid, and isolated as di‐sodium salt.Sodium hydrazinoethyl phosphate reacts with phenylisothiocyanate (in H2O+ethanol) to yield mainly the derivative thiocarbamoylated at the substituted nitrogen atom. This derivative, heated for one night at 100° in 0.5 N HCl, is cyclized to 3‐amino‐2‐phenylimino‐thiazolidine in 62% yield. Sodium hydrazinoethyl phosphate reacts with o‐methoxycarbonylphenyl isothiocyanate (in H2O+dioxane) at the unsubstituted nitrogen atom to yield mainly the corresponding quinazoline derivative (IV, X = OPO3Na2). This derivative, heated for one night at 100° in 0.5 N HCl, is cyclized to 2‐o‐carboxyphenylamino‐dihydro‐δ2‐1, 3, 4‐thiadiazine (Va) in 55% yield (hydrolysis of the lactamic function as well).Aminoethyl phosphorous monoester (colaminephosphorous acid) reacted with phenylisocyanate (in H20+dioxane) in slightly alkaline medium (one equivalent of NaOH) yields sodium N‐phenylcarbamoylaminoethyl phosphite. Refluxed for 20 minutes in 1N NaOH, this carbamoyl derivative is not cyclized but only hydrolyzed to the open‐chained N‐phenyl‐N′‐hydroxyethylurea (VII).