Substituted .alpha.-aminoacetamides and catalytic methods...

C - Chemistry – Metallurgy – 07 – D

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C07D 295/18 (2006.01) C07D 295/185 (2006.01) C08K 5/20 (2006.01) C09K 15/22 (2006.01) C09K 15/30 (2006.01) C10M 133/10 (2006.01) C10M 133/50 (2006.01)

Patent

CA 1110641

ABSTRACT OF THE DISCLOSURE Novel .alpha.-aminoacetamides are powerful stabilizers for organic materials subject to oxygen and heat degradation, and particularly for synthetic natural rubber and synthetic ester lubricants. A wide range of substituents on the amine and amide N atoms, and also on the saturated carbon atoms, yields an array of stabilizers having a wide range of compatibility in compositions comprising various synthetic resinous compounds to be stabilized. Novel synthesis are provided utilizing at least one amine nucleophilic agent, a dichlorocarbene ion generating agent, and an alkoxide ion generating agent, which together in the presence of aqueous alkali and an onium salt, yield novel .alpha.-aminoacetamides in which a wide choice of substituents may be introduced. The nucleo- philic agent may be a primary or secondary amine, or one of each. The dichlorocarbene ion generating agent is halo- form. the alkoxide ion generating agent may be a ketone, an aldehyde, or a cyanohydrin which reacts with the haloform. An .alpha.-trihalomethyl alcohol also reacts with the amine nucleophilic agent, without the benefit of a dichlorocarbene ion generating agent. When the alkoxide ion generating agent is an .alpha.-trihalomethyl alcohol, an .alpha.- hydrogen may optionally be substituted.

326317

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