--- title: "Passerini three-component reaction Template | MolDraw" url: https://www.moldraw.com/templates/passerini-reaction/ description: "Passerini three-component reaction template: Benzaldehyde, acetic acid and tert-butyl isocyanide combine: the isocyanide adds to the activated carbonyl…" lang: en publisher: Scidart Academy generated: 2026-11-13 --- [MolDraw](https://www.moldraw.com/) › [Templates](https://www.moldraw.com/templates/) › [Name reactions](https://www.moldraw.com/templates/name-reactions/) › Passerini three-component reaction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Passerini three-component reaction template ![Passerini three-component reaction template: Benzaldehyde, acetic acid and tert-butyl isocyanide combine: the isocyanide adds to the activated carbonyl carbon, acetate traps the nitrilium ion and an O → O acyl transfer gives the α-acyloxy amide.](https://www.moldraw.com/templates/passerini-reaction.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). Benzaldehyde, acetic acid and tert-butyl isocyanide combine: the isocyanide adds to the activated carbonyl carbon, acetate traps the nitrilium ion and an O → O acyl transfer gives the α-acyloxy amide. ## Mechanism step by step Aldehyde, carboxylic acid and isocyanide give an α-acyloxy amide 1. **Carbonyl activation** – Drawn stepwise; in aprotic solvents steps 1–3 are thought to be concerted 2. **α-Addition of the isocyanide** – The isocyanide carbon attacks the carbonyl carbon: a nitrilium ion 3. **Acetate adds** – An O-acyl imidate (isoimide) forms 4. **Acyl transfer** – The hydroxy group adds to the acyl C=O: a five-membered tetrahedral intermediate 5. **Collapse** – The C=O reforms and the ring C–O bond breaks: the acetyl group has moved O → O 6. **Proton transfer** – The imidate takes the proton: the amide ## Key points - The first isocyanide multicomponent reaction (Passerini, 1921): aldehyde or ketone + carboxylic acid + isocyanide → α-acyloxy carboxamide. - Fastest in aprotic solvents at high concentration and third order overall, which supports a non-ionic, H-bonded cyclic transition state (accepted mechanism); the ionic steps drawn here describe polar solvents. - The isocyanide carbon is attacked twice (α-addition), and the final acyl transfer is irreversible. - With an amine present the imine reacts instead of the aldehyde: the Ugi reaction (α-acylamino amide). Drawn with 144 atoms, 20 arrows, 10 shapes – every one editable in MolDraw. ## Sources - [Kürti & Czakó, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier 2005](https://openlibrary.org/isbn/9780124297852) Textbook - [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 16](https://openlibrary.org/isbn/9781119371809) 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 Passerini three-component reaction template free? You can preview the Passerini three-component reaction 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 Passerini three-component reaction 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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