--- title: "Curtius rearrangement Template – Chemistry Diagram | MolDraw" url: https://www.moldraw.com/templates/curtius-rearrangement/ description: "Curtius rearrangement template: Benzoyl azide (resonance form with N⁻–N⁺≡N) loses N₂ as phenyl migrates to nitrogen; methanol adds to the isocyanate to give…" lang: en publisher: Scidart Academy generated: 2026-10-28 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Curtius rearrangement [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Curtius rearrangement template ![Curtius rearrangement template: Benzoyl azide (resonance form with N⁻–N⁺≡N) loses N₂ as phenyl migrates to nitrogen; methanol adds to the isocyanate to give methyl N-phenylcarbamate.](https://www.moldraw.com/templates/curtius-rearrangement.webp) [Edit in MolDraw](https://www.moldraw.com/)Download with Pro Premium template. Preview and edit it free in MolDraw; downloading and exporting it is part of [MolDraw Pro](https://www.moldraw.com/pricing). Benzoyl azide (resonance form with N⁻–N⁺≡N) loses N₂ as phenyl migrates to nitrogen; methanol adds to the isocyanate to give methyl N-phenylcarbamate. ## Mechanism step by step An acyl azide loses N₂ and rearranges to an isocyanate, trapped as a carbamate 1. **Resonance form** – The acyl azide as N⁻–N⁺≡N 2. **Rearrangement** – Phenyl moves to N as N₂ leaves (concerted) 3. **Methanol adds** – Attack on the isocyanate carbon 4. **Proton transfer** – The carbamate ## Key points - The acyl azide comes from an acyl chloride and NaN₃ (or DPPA with the acid). - Migration keeps the configuration of the migrating carbon. - Water instead of an alcohol gives the amine (via the carbamic acid and loss of CO₂). - Related: Hofmann (N-bromoamide) and Lossen (hydroxamic acid) rearrangements. Drawn with 113 atoms, 14 arrows, 6 shapes – every one editable in MolDraw. ## Sources - [Curtius, Ber. Dtsch. Chem. Ges. 1890, 23, 3023](https://doi.org/10.1002/cber.189002302232) Original paper - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005](https://openlibrary.org/isbn/9780124297852) Textbook - [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012](https://openlibrary.org/isbn/9780199270293) Textbook ## How to use this template 1. Press **Edit in MolDraw**. The template opens on the canvas of the free MolDraw editor. 2. Change anything: move structures, edit atoms and labels, recolour highlights or delete what you do not need. 3. Add your own structures, arrows and text next to it, or combine several templates on one page. 4. Export the drawing as PNG, SVG or PDF for slides, worksheets, theses and papers. ## Frequently asked questions ### Is the Curtius rearrangement template free? You can preview the Curtius rearrangement template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates. ### Can I edit the Curtius rearrangement template? Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it. ### Is the chemistry checked? Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page. ### Which name reactions are included? 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