Method for preparing primary amide compounds from secondary or tertiary amides
AssigneeIndustry Foundation of Chonnam National University
InventorSun Woo Lee
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Abstract
The present invention relates to a method for preparing primary amides from tertiary or secondary amides substituted with various alkyl groups through a transamidation reaction without a metal catalyst in room-temperature conditions by adding ammonium carbonate ((NH4)2CO3), wherein the method is eco-friendly since various secondary and tertiary amides that are not toxic or corrosive are used as starting materials and ammonium carbonate ((NH4)2CO3) that is neither a strong acid nor a strong base is used, and the method is economical since various primary amides can be synthesized with an excellent yield at room temperature without a metal catalyst.
Claims11
A method for preparing a primary amide, the method comprising a step of:
- subjecting a secondary or tertiary amide as a substrate to transamidation with an ammonia source in absence of a catalyst,
- wherein the ammonia source is at least one selected from the group consisting of ammonium acetate, ammonium formate, and ammonium carbonate,
- wherein the transamidation is carried out in a temperature condition of 20 to 45° C., and wherein the substrate is selected from the group consisting of N-4-methoxyphenyl-N-tosyl benzamide, N-4-fluorophenyl-N-tosylbenzamide, N-benzyl-N-tosylbenzamide, N-methyl-N-tosylbenzamide, N-trifluoromethanesulfonyl-N-phenylbenzamide, N-mesityl-N-phenylbenzamide, N-Boc protected N-phenyl benzamide, N-benzoyl saccharin, N-benzoylsuccinimide, N-benzoylglutarimide, N-methyl-N-phenyl benzamide, and N,N-diphenylbenzamide,
- or the substrate is selected from the group consisting of 1-tosylpyrrolidin-2-one, 1-tosylpiperidin-2-one, and 1-tosylazepan-2-one.
A method for preparing a primary benzamide, the method including a step of:
- subjecting N-phenyl-N-tosyl benzamide as a substrate to transamidation with an ammonia source in absence of a catalyst,
- wherein the ammonia source is at least one selected from the group consisting of ammonium acetate, ammonium formate, and ammonium carbonate,
- wherein the transamidation is carried out in a temperature condition of 20 to 45° C.
A method for preparing a benzamide, the method including a step of:
- subjecting substituted N-phenyl-N-tosyl benzamide as a substrate to transamidation with an ammonia source in absence of a catalyst,
- wherein the ammonia source is at least one selected from the group consisting of ammonium acetate, ammonium formate, and ammonium carbonate,
- wherein the transamidation is carried out in a temperature condition of 20 to 45° C.
Dependencies are inferred from the claim text.