Amide formation

16 real reactions from the literature, on acid chlorides, anilines, primary amines and diketene. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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1. Amide formation: p-anisidine (an aniline) with Ac2O gives N-(4-methoxyphenyl)acetamide.

   Amide formationOrg. Synth. Coll. Vol. 3, p. 661

2. Amide formation: aniline and diketene with Δ; benzene gives acetoacetanilide (the amide).

   Amide formationOrg. Synth. Coll. Vol. 3, p. 10

3. Amide formation: piperidine (a secondary amine) with NaOH, H2O gives benzoylpiperidine (the amide).

   Amide formationOrg. Synth. Coll. Vol. 1, p. 99

4. Amide formation: methyl 10-chloro-10-oxodecanoate (an acid chloride) with NH4OH; 8 °C gives 9-carbamoyl-nonanoic acid methyl ester (the amide).

   Amide formationOrg. Synth. Coll. Vol. 3, p. 613

5. Amide formation: ethyl benzoylacetate (a β-keto ester) with xylene, Δ gives 3-oxo-3-phenylpropionanilide (the amide).

   Amide formationOrg. Synth. Coll. Vol. 3, p. 108

6. Amide formation: aniline with CH2Cl2 gives 2-methylacetanilide (the amide).

   Amide formationBioorg. Med. Chem. 2015, 23, 4638

7. Amide formation: phthaloyl chloride (an acid chloride) with 1); Et3N; CH2Cl2; 2) HCl / H2O gives tert-butyl 1,4-dioxo-2,3-benzoxazine-3-carboxylate (the amide).

   Amide formationOrg. Lett. 2016, 18, 3086

8. Amide formation: cyclohexanecarbonyl chloride (an acid chloride) with Et3N; CH2Cl2 gives N-methylcyclohexanecarboxamide.

   Amide formationJ. Org. Chem. 2007, 72, 7551

9. Amide formation: 5,5-dimethyl-3-(3-methylbenzoyl)imidazolidine-2,4-dione (an imide) with MeCN gives N,N-diethyl-m-toluamide.

   Amide formationEur. J. Org. Chem. 2018, 4436

10. Amide formation: p-toluidine (an aniline) with AcOH gives 4-methylacetanilide (the amide).

    Amide formationOrg. Synth. Coll. Vol. 1, p. 111

11. Amide formation: glycine (a primary amine) with Ac2O, H2O gives acetylglycine (the amide).

    Amide formationOrg. Synth. Coll. Vol. 2, p. 11

12. Amide formation: isobutyryl chloride (an acid chloride) with NH4OH gives isobutyramide.

    Amide formationOrg. Synth. Coll. Vol. 3, p. 490

13. Amide formation: ethyl lactate (an ester) with liquid NH3 gives lactamide.

    Amide formationOrg. Synth. Coll. Vol. 3, p. 516

14. Amide formation: glycine (a primary amine) with NaOH, H2O; 2) HCl gives hippuric acid (the amide).

    Amide formationOrg. Synth. Coll. Vol. 2, p. 328

15. Amide formation: cyclohexanecarbonyl chloride (an acid chloride) with (CH3)2NH; benzene gives N,N-dimethylcyclohexanecarboxamide.

    Amide formationOrg. Synth. Coll. Vol. 4, p. 339

16. Amide formation: aniline gives benzanilide (the amide).

    Amide formationOrg. Synth. Coll. Vol. 1, p. 82