Method for producing diaminobenzene compound

A kind of technology of diaminobenzene and compound is applied in the field of diaminobenzene compound to achieve the effects of improving yield, promoting dissolution and increasing solubility

Inactive Publication Date: 2019-12-27
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the existing technology, ther

Method used

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  • Method for producing diaminobenzene compound
  • Method for producing diaminobenzene compound
  • Method for producing diaminobenzene compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0183] Example 1 (Example of manufacturing diaminobenzene compound using aminonitrobenzene compound)

[0184] Carry out the following reaction.

[0185]

[0186] In a mixed solvent (reaction solvent) of dimethylformamide (DMF) (4ml), water (0.367ml, 20.4mmol) and toluene (3ml), methyl 2-amino-3-nitrobenzoate (1.0 g, 5.1mmol; 2-amino-3-nitrobenzene compound), sodium dithionite (purity 80% by mass) (3.33g, 15.3mmol ((the number of moles of sodium dithionite calculated from the purity)); Wako Pure Chemical Produced by the company, dithionite alkali metal salt), potassium carbonate (1.4g, 10.2 mmol; alkali metal carbonate) were stirred and mixed for 4 hours at a reaction temperature of 100°C (reaction time).

[0187] Water (14 mL) was added to the obtained reaction liquid, and then, the mixed liquid of the obtained reaction liquid and water was extracted with ethyl acetate (5 mL). The extraction based on this ethyl acetate (5 ml) was repeated 5 times. After washing the ethyl acetate s...

Example Embodiment

[0190] Example 2 (Example of manufacturing diaminobenzene compound using aminonitrobenzene compound)

[0191] Compared with Example 1, except for using sodium dithionite (purity 80% by mass) (2.22g, 10.2mmol ((the number of moles of sodium dithionite calculated from the purity)); Wako Pure Chemical Industries, the alkali of dithionite Metal salt), except for the reaction time of 5 hours, the same operation as in Example 1 was performed. The conversion rate was 10%. No polar impurities were confirmed.

Example Embodiment

[0192] Example 3 (Example of manufacturing diaminobenzene compound using aminonitrobenzene compound)

[0193] With respect to Example 1, except that the reaction solvent was a mixed solvent of DMF (7 ml) and water (0.099 ml, 5.1 mmol), the same operation as in Example 1 was performed. The yield of methyl 2,3-diaminobenzoate was 94%. The conversion rate is 100%. In addition, the purity of methyl 2,3-diaminobenzoate confirmed by HPLC was 95.4%, and the polar impurity was 2.5%. The analysis result of the obtained methyl 2,3-diaminobenzoate was the same as in Example 1.

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Abstract

The purpose of the present invention is to provide a method for easily producing a diaminobenzene compound and a benzimidazole compound at low cost. The present invention provides a method for producing a diaminobenzene compound or N-protected aminobenzene compound represented by formula (2), the method comprising bringing an aminonitrobenzene compound or N-protected nitrobenzene compound represented by formula (1) into contact with an alkali metal salt of dithionous acid. Also provided is said method in which a deprotection reaction is conducted according to need. (In formulae (1) and (2), nis an integer of 1-4; R1 is a C1-6 alkyl, C1-6 alkoxy, C2-6 acyloxy, C2-6 alkoxycarbonyl, or nitro group or a halogen atom, and when n>=2, then the R1 moieties may be the same or different; and RA isa hydrogen atom or a protective group.)

Description

technical field [0001] The present invention relates to a novel production method of diaminobenzene compounds useful as intermediates of chemical products, technical materials, and the like. Furthermore, it relates to a novel method of producing a benzimidazole derivative from the obtained diaminobenzene compound after producing the diaminobenzene compound by the production method. Background technique [0002] As intermediates of chemical products and original drugs, benzimidazole derivatives have very high utilization value. For example, benzimidazole derivatives represented by the following formula (5) have very high industrial utility value as intermediates of sartan active drugs such as candesartan cilexetil (see, for example, Patent Documents 1 to 3). [0003] [0004] (where, R 1 It is an alkyl group with 1 to 6 carbons, an alkoxy group with 1 to 6 carbons, an acyloxy group with 2 to 6 carbons, an alkoxycarbonyl group with 2 to 6 carbons, a nitro group or a halog...

Claims

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Application Information

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IPC IPC(8): C07C227/16C07C229/60C07D235/26
CPCC07C227/16C07C229/60C07D235/26Y02P20/55C07C229/56
Inventor 关雅彦田中健次
Owner TOKUYAMA CORP
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