Method for preparing amides from esters

A method for preparing an amide of the formula (I-1) or a diamide of the formula (I-2)

• where
• R1 is selected from the group consisting of hydrogen, C1-C30-alkyl which is unsubstituted or carries m radicals Ra, C1-C30-haloalkyl which is unsubstituted or carries m radicals Ra, C2-C30-alkenyl which is unsubstituted or carries m radicals Ra, C2-C30-haloalkenyl which is unsubstituted or carries m radicals Ra, C2-C30-alkynyl which is unsubstituted or carries m radicals Ra, C2-C30-haloalkynyl which is unsubstituted or carries m radicals Ra, C3-C30-cycloalkyl which is unsubstituted or carries m radicals Rb, C6-C22-aryl which is unsubstituted or carries m radicals Rb, and a 3- to 30-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring containing 1, 2, 3, or 4 heteroatoms or heteroatom groups selected from, N, O, S, SO, and SO2 as ring members, which is unsubstituted or carries m radicals Rb;
• R2 is C6-C22-aryl which is unsubstituted or carries m radicals Rb, or is a 5- to 30-membered heteroaromatic ring containing 1, 2, 3, or 4 heteroatoms selected from N, O, and S as ring members, where the heteroaromatic ring is unsubstituted or carries m radicals Rb;
• R3 is selected from the group consisting of hydrogen, C1-C30-alkyl which is unsubstituted or carries m radicals Ra, C1-C30-haloalkyl which is unsubstituted or carries m radicals Ra, C2-C30-alkenyl which is unsubstituted or carries m radicals Ra, C2-C30-haloalkenyl which is unsubstituted or carries m radicals Ra, C2-C30-alkynyl which is unsubstituted or carries m radicals Ra, C2-C30-haloalkynyl which is unsubstituted or carries m radicals Ra, C3-C30-cycloalkyl which is unsubstituted or carries m radicals Rb, C6-C22-aryl which is unsubstituted or carries m radicals Rb, and a 3- to 30-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring containing 1, 2, 3, or 4 heteroatoms or heteroatom groups selected from, N, O, S, SO, and SO2 as ring members, which is unsubstituted or carries m radicals Rb;
• or
• R3 forms a saturated or unsaturated 2-, 3-, or 4-membered linking group to a carbon or nitrogen ring atom of the aryl or heteroaromatic ring R2;
• where the linking group may comprise 1 or 2 heteroatoms or heteroatom groups selected from, N, O, S, SO, and SO2;
• where the linking group may carry 1, 2, or 3 radicals selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
• A is a divalent aliphatic, cycloaliphatic, aliphatic-cycloaliphatic aromatic, aromatic-aliphatic, or heterocyclic moiety;
• each Ra is independently selected from the group consisting of cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C(═O)Rc, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, C3-C20-cycloalkyl, C6-C22-aryl which is unsubstituted or carries m radicals Rd, and a 3- to 20-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring containing 1, 2, 3, or 4 heteroatoms or heteroatom groups selected from, N, O, S, SO, and SO2 as ring members, which is unsubstituted or carries m radicals Rd;
• each Rb is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, NReRf, C(═O)NReRf, C1-C20-alkyl, C1-C20-haloalkyl, C2-C20-alkenyl, C2-C20-haloalkenyl, C2-C20-alkynyl, C2-C20-haloalkynyl, C3-C20-cycloalkyl, C6-C22-aryl which is unsubstituted or carries m radicals Rd, and a 3- to 20-membered saturated, partially unsaturated, or maximally unsaturated heterocyclic ring containing 1, 2, 3, or 4 heteroatoms or heteroatom groups selected from, N, O, S, SO, and SO2 as ring members, which is unsubstituted or carries m radicals Rd;
• each Rc is independently selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkyl which carries a group NReRf, C1-C4-alkoxy, and C1-C4-haloalkoxy;
• each Rd is independently selected from the group consisting of halogen, cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
• each Re is independently selected from the group consisting of hydrogen and C1-C4-alkyl;
• each Rf is independently selected from the group consisting of —C(═O)-phenyl and phenyl which is unsubstituted or substituted by 1, 2, or 3 radicals selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy;
• each m is independently 1, 2, 3, 4, or 5;
• comprising reacting an ester compound (II) of formula (II-1) or (II-2)
• wherein
• R1 and A are as defined above;
• and
• R4 is selected from the group consisting of C1-C30-alkyl, C6-C14-aryl, and C6-C14-aryl-C1-C4-alkyl;
• with an amine of formula (III)
• wherein R2 and R3 are as defined above,
• in the presence of an alkali metal-containing base and a Lewis acid;
• where the reaction is carried out under anhydrous conditions, where a water content in the reaction mixture is at most 0.15% by weight, relative to a total weight of the reaction mixture.