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Process for preparing 1,2,4-benzothiadiaxine-1,1-dioxide compound

A technology of dioxo compounds and benzothiadiazine, which is applied in the field of preparation of 1,2,4-benzothiadiazine-1,1-dioxo compounds, can solve the problem of low yield in the cyclization process, Problems such as low yield and long number of processes

Inactive Publication Date: 2006-10-25
FUJIFILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these reactions all have the so-called problem of requiring high reaction temperature.
J.Org.Chem., 16,815 (1951) also describes the method of making 2-aminobenzenesulfonamide compound and orthoester compound react, but there is the problem of so-called low yield
In addition, as described in Chemical World, 21, 235 (1999), there is also a method of cyclizing the 2-aminobenzenesulfonamide compound with an acylating agent and then cyclizing it with phosphorus oxychloride, but there are so-called long steps, In addition, when the acyl moiety contains a functional group, the yield of the cyclization step is low

Method used

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  • Process for preparing 1,2,4-benzothiadiaxine-1,1-dioxide compound
  • Process for preparing 1,2,4-benzothiadiaxine-1,1-dioxide compound
  • Process for preparing 1,2,4-benzothiadiaxine-1,1-dioxide compound

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preparation example Construction

[0117] In the preparation method of the present invention, the process of synthesizing the compound represented by the general formula (I) itself in the synthesis stage of the compound represented by the general formula (III) can also be used without separating intermediates in the way, or similarly using simple extraction, Preparation by concentrating the reaction solution, etc.

[0118] Specifically, after the reaction of o-nitrobenzenesulfonyl chlorides and amines, the starting material for the synthesis of the compound represented by the general formula (III), the nitro group can be reduced without separation and the resulting general formula (III) can be separated. Represented aniline compound, then make it react with the compound represented by general formula (IV) or (V), without separating the intermediate represented by general formula (II), carry out continuous reaction once synthetic general by - pot method (same reaction tank) The compound represented by the formul...

Embodiment 1

[0132] Synthesis of Exemplified Compound (8)

[0133] Exemplary compound (8) was synthesized as follows.

[0134] 【Chemical 32】

[0135]

[0136] To 10.0g (23.6mmol) compound (A-1), 5.32g (28.3mmol) 3,3-diethoxy ethyl acrylate (A-0) and 0.045g (0.24mmol) p-toluenesulfonic acid monohydrate 20ml of toluene was added, heated to reflux for 30 minutes. After adding 0.226 g (2.4 mmol) of sodium tert-butoxide, it was heated to reflux for 5 hours. After cooling the reaction solution to room temperature, dilute hydrochloric acid was added for neutralization, and 30 ml of ethyl acetate was added. The organic solvent layer was washed with water, dried over sodium sulfate, and the solvent was distilled off under reduced pressure. Crystallization from methanol gave 11.2 g of the target exemplified compound (8). Yield 91.1%. Melting point: 80-81°C.

[0137] 1 H-NMR (300MHz, CDCl 3 )11.72(s, 1H), 778(d, 1H), 7.58(t, 1H), 7.19(t, 1H), 7.10(d, 1H), 4.61(s, 1H), 4.20(q, 2H), 2.27(...

Embodiment 2

[0138] Synthesis of Exemplified Compound (8)

[0139] Add 20ml of xylene to 8.49g (20mmol) of compound (A-1), 4.54g (24mmol) of 3,3-diethoxy ethyl acrylate (A-0) and 0.60g (6.52mmol) of acetic acid, and heat to reflux 30 minutes. After addition of 3.04 g (20 mmol) DBU, it was heated to reflux for 7 hours. After cooling to room temperature, dilute hydrochloric acid was added for neutralization, and 30ml of ethyl acetate was added. After washing with water, the organic solvent layer was dried with sodium sulfate. After the solvent was distilled off under reduced pressure, 8.78 g of the target exemplary compound (8) were obtained by crystallization from methanol. Yield 84.0%.

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Abstract

A method of producing 1,2,4-benzothiadiazine-1,1-dioxide compound of formula (I), including reacting a 2-aminobenzenesulfonamide compound with a 1,1-dialkoxyalkene compound or with an orthoester compound, in the presence of an acid, to obtain an iminoether compound, and then subjecting the iminoether compound to a ring closure reaction, in the presence of a base: <CHEM> wherein, in formula (I), R1 is an alkyl group, or an aryl group; R2 is a substituent; n is 0 to 4; and R3 is a hydrogen atom or a substituent.

Description

technical field [0001] The present invention relates to 1,2,4-benzothiadiene useful as a coupler for forming a yellow pigment in a silver halide photographic photosensitive material or its synthetic intermediate, as well as a synthetic intermediate of pigment, medicine, agricultural chemical or electronic material, etc. Process for the preparation of oxazine-1,1-dioxo compounds. Background technique [0002] As described in U.S. Patent No. 3841880, 1,2,4-benzothiadiazine-1 having a substituted or unsubstituted alkyl or aryl group at the 2-position and a substituted or unsubstituted alkyl group at the 3-position, The 1-dioxo compound is useful as a coupler for forming a yellow pigment in a silver halide photographic photosensitive material and its intermediate, or as a synthetic intermediate for pigments, medicines, agricultural chemicals or electronic materials. [0003] As a method for synthesizing these compounds, the synthesis of 3-ethoxycarbonylmethyl-1 by reacting 2-am...

Claims

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Application Information

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IPC IPC(8): C07D285/24C07B61/00C07D285/30C07D417/06
CPCC07D285/24C07D285/30C07D417/06
Inventor 金子祐士元木益司山川一义森英登安冈宏
Owner FUJIFILM CORP
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