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Catalytic Methoxycarbonylation of Aromatic Diamines with Dimethyl Carbonate to Their Dicarbamates Using Zinc Acetate

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Abstract

The methoxycarbonylation of 2,4-toluene diamine and 4,4′-diphenylmethane diamine with dimethyl carbonate to the corresponding dicarbamates using zinc acetate was carried out at 453 K. Zn(OAc)2, prepared by evacuating Zn(OAc)2⋅2H2O at 383 K for 2 h, yields dimethyltoluene-2,4-dicarbamate in 96% yield in 2 h, while Zn(OAc)2⋅2H2O yields dimethyl-4,4′-methylenediphenyldicarbamate in 98% yield at 453 K in 2 h.

The structure of methyl 3-amino-4-methyl phenyl carbamate, which is one of the intermediates for the reaction of 2,4-toluene diamine with dimethyl carbonate into dimethyltoluene-2,4-dicarbamate, has been determined by measuring the NOE spectrum of 1H NMR.

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Baba, T., Kobayashi, A., Yamauchi, T. et al. Catalytic Methoxycarbonylation of Aromatic Diamines with Dimethyl Carbonate to Their Dicarbamates Using Zinc Acetate. Catalysis Letters 82, 193–197 (2002). https://doi.org/10.1023/A:1020566928295

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  • DOI: https://doi.org/10.1023/A:1020566928295

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