Method for making acylamides by synthesizing and acylating...

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

Reexamination Certificate

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Reexamination Certificate

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06977299

ABSTRACT:
A method is provided for synthesizing acylamides, useful as protectant for cultivated plants. A benzoxazine, such as 3,4-dihydro-3-methyl-2H-1,4-benzoxazine, is made in a stepwise manner by initially forming an o-nitrophenoxyketone by reacting a haloketone and a nitrophenol. The o-nitrophenoxyketone is hydrogenated to form the corresponding benzoxazine, which is thereafter acylated with an acylhalide to produce the acylamide, such as 4-dichloroacetyl-3,4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine.

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patent: 4618361 (1986-10-01), Moser
patent: 5977167 (1999-11-01), Koga et al.
Fujimoto et al., “Preparation of benzoxazine derivatives as intermediates for bactericides”, Chemical Abstracts, vol. 116, No. 13, 1992.
Fukushima et al., “Preparation of 6-amino-7-fluoro-2H-1, 4-benzoxazin-3(4H)-o ne as intermediate for herbicides”, Chemical Abstracts, vol. 119, No. 15, 1993.

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