A New Cyanoacetamide Synthesis in Liquid Ammonia Alkylation of Cyanoacetamide with Alkali Hydroxide

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概要

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• In the former report^<(1)> the authors have reported on malondiamide synthesis with liquid ammonia-alkali hydroxide. The metalation in cyanoacetamide and malononitrile having strongly active methylene group like malondiamide was found to be successful with alkali hydroxide in liquid ammonia, reaction of them with alkyl halide gave alkyl cyanoacetamide and alkyl malononitrile. The method was named as cyanoacetamide synthesis with alkali hydroxide in liquid ammonia. The experiments were performed in liquid ammonia at room temperature, using lithium, sodium and potassium hydroxides and then the products were alkylated with benzyl, ethyl, propyl and butyl halides. A large amount of di-alkyl compounds were produced in addition to monoalkyl compounds. These results are same with that of cyanoacetamide synthesis with alkali amide in liquid ammonia. The speciality of the method is same with that of malondiamide synthesis and summarized with the following reaction formulas. NaOH (in NH_3) + NH_3 〓 NaNH_2 + H_2O (in NH_3) H_2O (in NH_3) + NH_3→ NH_4OH CH_2 〓CN CONH_2 + NaNH_2 〓[CH〓CN CONH_2]^-Na^+ + NH_3 [CH〓CN CONH_2]^- + RX →CHR〓CN CONH_2 + X^- [CR〓CN CONH_2]^- + RX →CRR〓CN CONH_2 + X^-

• 東北大学の論文

著者

• Shimo Kotaro

  Department Of Chemistry Defense Academy:the Chemical Research Institute Of Non-aqueous Solutions

• ASAMI Ryuzo

  The Chemical Research Institute of Non-Aqueous Sotutions

• Asami Ryuzo

  The Chemical Research Institute Of Non-aqueous Solutions

関連論文

• A New Malondiamide Synthesis in Liquid Ammonia Alkylation of Malondiamide with Alkali Hydroxide
• A New Cyanoacetamide Synthesis in Liquid Ammonia Alkylation of Cyanoacetamide with Alkali Hydroxide
• Cyanoacetamide Synthesis in Liquid Ammonia
• Organic Syntheses in Non-Aqueous Solutions. II The Alkylation of Glycine Derivatives in Liquid Ammonia. Part II : Benzylation and Methylation of Glycine Anhydride in Liquid Ammonia
• Malondiamide Synthesis in Liquid Ammonia
• On the Beckmann Rearrangement in Liquid Sulfur Dioxide. I : Synthesis of ε-Caprolactam

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