Die Umwandlung von Aminen in Trifluoracetamide (1) gelingt mit N‐Trifluoracetyl‐Nylon 66, das bei der Reaktion in Nylon 66 übergeht. Nylon 66 läßt sich einfach abfiltrieren.
The N-X bond of positive halogen compounds (I) can be readily methylenated at 15" with diazomethane to give the N-halogenomethyl derivatives (111). not isolated as such but directly condensed with nucleophiles [sodium pnitrophenoxide, diethyl phthalimido(sodio)malonate, and morpholine] ; the parent N-H compounds (VII) are formed as secondary products. This new reaction has been applied to N-halogeno-N-substituted carboxamides, sulphonamides, phosphoramides, and urethanes. The mechanism of the methylene insertion into the N-X linkage Nacional de La Plata, La Plata, Argentina is discussed.
N(3)-Substituted hydantoins bearing a variety of substituents a t position 5 have been N ( l )-alkylated a t room temperature by treatment with several types of alkyl halide or tosylate in anhydrous NN-dimethylformamide containing sodium hydride. The method shows a wide applicability, giving good yields with or without activating groups a t position 5.IN a preliminary communication we described the formation of N ( 1)-alkyl derivatives of N(3)-unsubstituted hydantoins from the pre-formed hydantoin system. This route involves three steps: (1) introduction of an aminomethyl group to protect position 3; (2) alkylation at position 1 with an alkyl halide in NN-dimethylformamide (DMF) containing sodium hydride at room temperature; and (3) hydrolytic elimination of the protecting group at room temperature.Step (1) has been studied previously ;under appropriate conditions selective aminomethylation at the more reactive position 3 can be accomplished in high yield. However, little information is available with regard to the subsequent steps. The present paper deals with the scope of the N(1)-alkylation method [step (2)].It has been stated4 that hydantoins can generally be alkylated in basic medium at position 3 but not a t posi-1
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