Method for producing n-benzyl-2-bromo-3-methoxypropionamide and intermediates thereof
The present invention provides an industrially-preferable method for safely producing N-benzyl-2-bromo-3-methoxypropionamide at a high yield but at low cost. The method for producing of the present invention includes: in sequence, an amidation process that causes diacrylic anhydride to react with benzylamine in a solvent to obtain N-benzylacrylamide; a bromination process that causes N-benzylacrylamide to react with bromine in a solvent to obtain N-benzyl-2,3-dibromopropionamide; and a methoxylation process that causes N-benzyl-2,3-dibromopropionamide to react with methanol in the presence of a base to obtain N-benzyl-2-bromo-3-methoxypropionamide.
1. A method for producing N-benzyl-2-bromo-3-methoxypropionamide comprising:
in sequence,
an amidation process that causes diacrylic anhydride to react with benzylamine in a two-phase system including an organic-solvent phase and an aqueous phase comprising an inorganic or organic base to obtain N-benzylacrylamide;
a bromination process that causes N-benzylacrylamide to react with bromine in a solvent to obtain N-benzyl-2,3-dibromopropionamide; and
a methoxylation process that causes N-benzyl-2,3-dibromopropionamide to react with methanol in the presence of a base to obtain N-benzyl-2-bromo-3-methoxypropionamide.
2. The method according to claim 1 , wherein diacrylic anhydride used in the amidation process is obtained by causing acrylic acid to react with a condensation agent in a solvent.
3. A method for producing N-benzyl-2,3-dibromopropionamide comprising:
in sequence,
an amidation process that causes diacrylic anhydride to react with benzylamine in a two-phase system including an organic-solvent phase and an aqueous phase comprising an inorganic or organic base to obtain N-benzylacrylamide; and
a bromination process that causes N-benzylacrylamide to react with bromine in a solvent to obtain N-benzyl-2,3-dibromopropionamide.
4. The method according to claim 3 , wherein the condensation agent is a carbodiimide-based condensation agent.
5. A method for producing N-benzylacrylamide comprising an amidation process that causes diacrylic anhydride to react with benzylamine in a two-phase system including an organic-solvent phase and an aqueous phase comprising an inorganic or organic base to obtain N-benzylacrylamide.
6. The method according to claim 5 , wherein diacrylic anhydride used in the amidation process is obtained by causing acrylic acid to react with a condensation agent in a solvent.
7. The method according to claim 6 , wherein the condensation agent is a carbodiimide-based condensation agent.
8. The method of claim 1 wherein the aqueous phase comprises an inorganic base.
9. The method of claim 3 wherein the aqueous phase comprises an inorganic base.
10. The method of claim 5 wherein the aqueous phase comprises an inorganic base.