Chem. J. Chinese Universities ›› 1984, Vol. 5 ›› Issue (5): 653.

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The Preparation of Some N-Mannich Bases of Bicyclo(2,2,1) Hept-5-ene-1,4,5,6,7,7-Hexachloro-2,3-Dicarboximide

Yuan Qibin, Chen Guangxu, Xu Xiujuan   

  1. Department of Chemistry, Beijing Normal University, Beijing
  • Received:1983-02-23 Online:1984-10-24 Published:1984-10-24

Abstract: Bicyclo(2,2,1)hept-5-ene-1,4,5,6,7,7-hexachloro-2,3-dicarboximide has been prepared by fusing bicyclo(2,2,1)-hept-5-ene-1,4,5,6,7,7-hexachloro-2,3-dicarboxylic anhydride with urea. This imide reacts with formaldehyde and arnine(aromatic as well as aliphatic) in ethyl alcohol at room temperature to give N-Mannich bases in good yields. Twenty-four such bases, of which twenty-two are new compounds, were prepared by this method except No. 11 and 13 (see table). At room temperature, p-nitroariline or o-nitroaniline reads with this imide and formaldehyde yielding the bis(p-nitrophenylamino)methane or bis(o-nitrophenylamino) methane. When they are refluxtd for one hour, the expected N-Mannich bases were also obtained.These N-mannich bases can also be obtained by first converting the imide to the N-hydroxymethyl derivative followed by treatment with amine.It was found that the imide can also react with the amine-formaldehyde condensation product to yield N-Mannich bases without the aid ofexternally added acid.

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