Preparation method of benzoylsulfamoyl benzamide and preparation intermediate

A kind of technology of benzoyl sulfamoyl benzamide and methoxy group, which is applied in the field of preparing intermediates

Pending Publication Date: 2020-08-11
HEBEI LANSHENG BIOTECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Same as above, the above-mentioned method of CN105636942A also has the side

Method used

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  • Preparation method of benzoylsulfamoyl benzamide and preparation intermediate
  • Preparation method of benzoylsulfamoyl benzamide and preparation intermediate
  • Preparation method of benzoylsulfamoyl benzamide and preparation intermediate

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preparation example Construction

[0034] The new preparation method of the present invention comprises:

[0035] step one:

[0036]

[0037] Step two:

[0038]

[0039] The reaction in the above step 1 can be carried out in solvents such as halogenated hydrocarbons, toluene, isopropyl acetate, ethyl acetate, tetrahydrofuran, dioxane, etc., and is particularly preferably carried out in dichloromethane. The reaction temperature is generally 15°C to 60°C, preferably 25°C to 35°C. The reaction time is 1 to 8 hours, preferably 1 to 6 hours. The molar ratio of the compound of formula (I) to pivaloyl chloride is preferably 1:1-1:2, more preferably 1:1-1:1.5, particularly preferably 1:1-1:1.1.

[0040] The reaction of step 1 is preferably carried out in the presence of a base. The base is preferably an organic base, including but not limited to triethylamine, diisopropylethylamine, pyridine, etc., preferably triethylamine. The amount of the base used is preferably 1 to 3 times the molar amount of the compou...

Embodiment 1

[0068] The preparation of embodiment 1N-(2-methoxy-benzoyl)-4-methyl-benzenesulfonamide

[0069]

[0070] Add 250 grams of isopropyl acetate to the three-necked flask, start stirring, add 110 grams of p-toluenesulfonamide, raise the temperature to 75°C to 80°C, then add 112.4 grams of o-methoxybenzoyl chloride dropwise, and the dropwise addition is completed in about 1 hour . After dropping, keep warm for 3 hours. Sampling was carried out for HPLC detection, and the remaining p-carboxybenzenesulfonamide was ≤0.5%, and the reaction was qualified. Cool down to 25°C, filter, rinse with 50 g of isopropyl acetate, and dry to obtain 187 g of the target product.

Embodiment 2

[0071] Example 2 Preparation of 4-(2-methoxy-benzoylsulfonyl)-benzoic acid

[0072]

[0073] First add 1500 grams of water in the three-necked flask, start stirring, add 187 grams of N-(2-methoxy-benzoyl)-4-methyl-benzenesulfonamide prepared in Example 1, and then add 49 grams sodium hydroxide. Control the temperature in a cold water bath to 25°C to 30°C, slowly add 194 grams of potassium permanganate, and dropwise complete in about 2 hours. After the addition was completed, the reaction was continued at 25°C to 30°C for 2h. Manganese dioxide was removed by filtration, and the filtrate was adjusted to pH 3-4 with hydrochloric acid, filtered, washed with water, and dried to obtain 191 grams of the product.

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Abstract

The invention provides a preparation method of benzoylsulfamoyl benzamide. The method comprises the following steps: reacting a sulfamoyl benzoic acid compound as shown in formula (I) with pivaloyl chloride so as to generate an anhydride compound as shown in formula (II), and reacting the anhydride compound with amine. In the formulas, R1 is hydrogen, halogen, a C1-10 alkyl group, a C1-10 alkoxy group, a C3-8 cycloalkyl group, a C3-8 cycloalkoxy group, a halogenated C1-10 alkyl group, a halogenated C1-10 alkoxy group, a halogenated C3-8 cycloalkyl group or a halogenated C3-8 cycloalkoxy group,and R2 and R3 each independently represent hydrogen, a C1-10 alkyl group, or a C3-8 cycloalkyl group. The invention also relates to compounds as shown in the formula (II) and application of the compounds as intermediates for the preparation of compounds as shown in formula (III).

Description

technical field [0001] The invention relates to a preparation method and an intermediate of benzoylsulfamoylbenzamide. Background technique [0002] Chinese patents CN1272106A, CN1812962A, CN105636942A and CN107683276A serial applications disclose the preparation method of acylsulfamoylbenzamide. [0003] Specifically, CN1272106A discloses the following methods a and b, wherein method a is specifically implemented, and method b is only mentioned in general. [0004] Method a: [0005] [0006] Method b: [0007] [0008] CN1812962A discloses following method: [0009] [0010] In the above method disclosed by CN1812962A, the sulfamoyl carboxylic acid compound of formula (II) reacts with chlorinating agent earlier to generate the following activated acid chloride compound, and this compound can have a side reaction with the compound of formula (II). will combine. Although it is described in CN1812962A that the above method can basically avoid the generation of u...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/51
CPCC07C303/40C07C311/51C07C2601/02Y02P20/55
Inventor 张志虎刘伟伟郭红永王浩褚倩倩
Owner HEBEI LANSHENG BIOTECH CO LTD
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