Convert metanamine to formic acid
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CH3-COOH + SOCl2 → CH3-COCl (acetyl chloride)
CH3-COCl + NaN3 → CH3-CO-N3 (acetyl azide)
CH3-CO-N3 + heat or light → CH3-CO-N (acetylnitrene — an unstable intermediate) → CH3-NCO (methyl isocyanate)
CH3-NCO + H2O→ CH3-NH2 (methylamine) + CO2
There are some alternatives to this process, all going via that acetyl azide and/or acetylnitrene intermediate. What I’ve shown is the Curtius reaction. The Schmidt reaction is acid-catalyzed and has a different mechanism, and occurs via a protonated acyl azide. In the Hofmann reaction, the acylnitrene is made by treating acetamide with bromine under alkaline conditions, giving a CH3-CO-NHBr intermediate.
CH3-COCl + NaN3 → CH3-CO-N3 (acetyl azide)
CH3-CO-N3 + heat or light → CH3-CO-N (acetylnitrene — an unstable intermediate) → CH3-NCO (methyl isocyanate)
CH3-NCO + H2O→ CH3-NH2 (methylamine) + CO2
There are some alternatives to this process, all going via that acetyl azide and/or acetylnitrene intermediate. What I’ve shown is the Curtius reaction. The Schmidt reaction is acid-catalyzed and has a different mechanism, and occurs via a protonated acyl azide. In the Hofmann reaction, the acylnitrene is made by treating acetamide with bromine under alkaline conditions, giving a CH3-CO-NHBr intermediate.
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