--- title: "Ugi four-component reaction Template | MolDraw" url: https://www.moldraw.com/templates/ugi-reaction/ description: "Ugi four-component reaction template: Benzaldehyde and methylamine form an imine; acetic acid protonates it, tert-butyl isocyanide adds to the iminium ion (a…" 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/) › Ugi four-component reaction [Name reactions](https://www.moldraw.com/templates/name-reactions/)Premium # Ugi four-component reaction template ![Ugi four-component reaction template: Benzaldehyde and methylamine form an imine; acetic acid protonates it, tert-butyl isocyanide adds to the iminium ion (a nitrilium ion), acetate traps it and the Mumm rearrangement moves the acetyl group from O to N.](https://www.moldraw.com/templates/ugi-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 and methylamine form an imine; acetic acid protonates it, tert-butyl isocyanide adds to the iminium ion (a nitrilium ion), acetate traps it and the Mumm rearrangement moves the acetyl group from O to N. ## Mechanism step by step Aldehyde, amine, carboxylic acid and isocyanide combine to an α-acylamino amide 1. **Imine formation** – The amine adds to the C=O and water is lost (see Imine formation) 2. **Protonation** – The carboxylic acid protonates the imine: an iminium ion and acetate 3. **α-Addition of the isocyanide** – The isocyanide carbon lone pair attacks the iminium carbon: a nitrilium ion 4. **Acetate adds** – Addition to the nitrilium carbon gives an O-acyl imidate 5. **Mumm rearrangement** – The amine nitrogen adds to the ester C=O: a five-membered tetrahedral intermediate 6. **Collapse: acyl now on N** – The C=O reforms and the ring C–O bond breaks: O → N acyl transfer 7. **Proton transfer** – The imidate takes the N–H proton: the second amide ## Key points - Four components, one pot (usually MeOH, room temperature): only water is lost, so the reaction is highly atom-economical. - The isocyanide carbon is both nucleophile and electrophile (α-addition): it bonds to the iminium carbon and then to the carboxylate oxygen. - The Mumm rearrangement (O → N acyl transfer) is irreversible and pulls all the earlier equilibria through. - Product: a peptide-like bis-amide with a new stereocentre (racemic unless a chiral component is used); varying the four inputs builds combinatorial libraries. Drawn with 169 atoms, 21 arrows, 11 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 Ugi four-component reaction template free? You can preview the Ugi four-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 Ugi four-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? Over seventy, covering the reactions most often asked in school-leaving exams (A-level, IB, CBSE, JEE and NEET) and first-year university courses, including condensations, rearrangements, oxidations, reductions and aromatic substitutions. ## More name reactions templates [**Fischer esterification**Free · Name reactions](https://www.moldraw.com/templates/fischer-esterification/)[**Grignard addition to a ketone**Free · Name reactions](https://www.moldraw.com/templates/grignard-addition/)[**Michael addition**Free · Name reactions](https://www.moldraw.com/templates/michael-addition/)[**Diels–Alder reaction**Premium · Name reactions](https://www.moldraw.com/templates/diels-alder/)[**Friedel–Crafts acylation**Premium · Name reactions](https://www.moldraw.com/templates/friedel-crafts-acylation/)[**Claisen condensation**Premium · Name reactions](https://www.moldraw.com/templates/claisen-condensation/)[**Friedel–Crafts alkylation**Premium · Name reactions](https://www.moldraw.com/templates/friedel-crafts-alkylation/)[**Cannizzaro reaction**Premium · Name reactions](https://www.moldraw.com/templates/cannizzaro-reaction/) ## Related pages [**Curved Arrow Mechanism Worksheet**Free printable worksheet](https://www.moldraw.com/educational-materials/curved-arrow-mechanism-worksheet/)[**Predict the Product Worksheet: Organic Reactions**Free printable worksheet](https://www.moldraw.com/educational-materials/predict-the-product-worksheet/)[**All Name reactions templates**93 templates](https://www.moldraw.com/templates/name-reactions/)[**All chemistry templates**525 templates in 31 categories](https://www.moldraw.com/templates/) MolDraw Pro Download all 525 templates - Export the 437 premium templates as PNG, SVG or PDF - AI chemistry assistant - Structure scanning from images - Cloud save and teaching slides [See Pro plans](https://www.moldraw.com/pricing) Free templates stay free. 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