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Preparation method of substituted benzene sulfonyl chloride

A technology of benzenesulfonyl chloride and acyl chloride, applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problems of high requirements for reaction equipment, unfavorable industrial production, and long reaction steps, so as to achieve easy control of the reaction and reduce the discharge of "three wastes", equipment less demanding effect

Active Publication Date: 2014-04-23
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The literature on the report of n-butyllithium method (Penoxsulam-Structure-activity relationships of triazolopyrimidine sulfonamides. Bioorganic & medicinal chemistry, 2009, 17(12): 4230-4240), the reaction steps of this method are long, the cost is high, and the It is carried out at low temperature (-78°C), which requires high reaction equipment and is not conducive to industrial production. The reaction process is as follows

Method used

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  • Preparation method of substituted benzene sulfonyl chloride
  • Preparation method of substituted benzene sulfonyl chloride
  • Preparation method of substituted benzene sulfonyl chloride

Examples

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Embodiment 1

[0027] The preparation of embodiment 1 p-chlorobenzenesulfonyl chloride

[0028] Add 12.7g of p-chloroaniline into a three-necked flask containing 25.4g of 75% sulfuric acid, place the three-necked flask in an ice bath, and slowly add 20mL of sodium nitrite aqueous solution (5.5mol L -1 ), after the dropwise addition was completed, the reaction was stirred for 20 min to obtain a diazonium salt solution.

[0029] Add 23.8g of thionyl chloride into a constant pressure dropping funnel, slowly drop it into a double-necked flask filled with 14.5mL of water under an ice bath, add 2.69g of copper chloride after the drop, and then use glue under ice bath conditions. The diazonium salt solution was quickly added to the aqueous solution with a head dropper, and then stirred at room temperature for 20 min. The pH of the system was adjusted to 2 with saturated potassium carbonate solution, extracted several times with ethyl acetate, and 16.5 g of a light yellow solid was obtained by rota...

Embodiment 2

[0030] Embodiment 2 Preparation of p-chlorobenzenesulfonyl chloride

[0031] Add 12.7g of p-chloroaniline into a three-necked flask filled with 38.1g of concentrated hydrochloric acid, place it in an ice bath, control the temperature at about 0-5°C, and slowly add 20mL of sodium nitrite aqueous solution (6.0mol L -1 ), keep the temperature below 5°C during the dropwise addition, and stir for 60 min to obtain a diazonium salt solution.

[0032] Add 35.7g of thionyl chloride into the constant pressure dropping funnel, slowly drop it into a double-necked flask filled with 29mL of water under an ice bath, add 0.99g of cuprous chloride after dropping, and then use a rubber-tip dropper to drop the heavy Nitrogen salt solution was quickly added to the aqueous solution, and then stirred at room temperature for 20 min, extracted several times with ether, adjusted to pH 4 with saturated potassium carbonate solution, and rotary evaporated to obtain a light yellow solid with a yield of 91...

Embodiment 3

[0033] Example 3 Preparation of 2-nitro-4-chlorobenzenesulfonyl chloride

[0034] Add 17.3g of 2-nitro-4-chloroaniline into a three-necked flask containing 103.8g of concentrated hydrochloric acid, place it in an ice bath, control the temperature at about -5 to 0°C, and slowly add 20mL of sodium nitrite aqueous solution (5.25 mol L -1 ), keep the temperature below 0°C during the dropwise addition, and stir for 20 minutes to obtain a diazonium salt solution.

[0035] Add 59.5g of thionyl chloride into the constant-pressure dropping funnel, slowly drop it into a double-necked flask containing 116mL of water under an ice bath, add 0.8g of cuprous chloride after dropping, and then use a rubber-tip dropper to remove the heavy Nitrogen salt solution was quickly added to the aqueous solution, and after completion, stirred at room temperature for 10 min, extracted several times with dichloromethane, adjusted the pH to 8 with saturated potassium carbonate solution, and rotary evapor...

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Abstract

The invention provides a preparation method of a pesticide intermediate, and in particular relates to a preparation method of substituted benzene sulfonyl chloride. The preparation method comprises the following steps: by taking substituted aniline as a raw material, first, carrying out diazo-reaction with sodium nitrite; then, carrying out chlorosulfonation with thionyl chloride aqueous liquor containing a catalyst to prepare substituted benzene sulfonyl chloride, wherein the yield ranges from 78% to 91%. The preparation method provided by the invention simplifies the reaction step, is safe to operate, mild in reaction conditions which are easy to control and low in equipment demand, the yield is improved, the production cost is lowered, emission of the three wastes is reduced, and the environment-friendly load is reduced, so that the preparation method is suitable for industrialized production.

Description

technical field [0001] The invention relates to the technical field of preparation of pesticide intermediates, in particular to a preparation method of substituted benzenesulfonyl chloride represented by general formula (2). [0002] [0003] In the formula, R 1 , R 2 Represented as a hydrogen atom, a halogen atom, a nitro group, an alkyl group or an alkyl group substituted by a halogen atom. Background technique [0004] Sulfonylurea and sulfonamide herbicides are widely used as plant acetolactate synthase (ALS) inhibitors for weed control. These two types of herbicides have the advantages of small dosage, wide herbicidal spectrum, high selectivity, and safety to mammals. They are the second-largest products in sales after carbamates, and have attracted the attention of pesticide developers. Substituted benzenesulfonyl chlorides are important intermediates in the synthesis of these two types of herbicides. [0005] At present, in the synthesis of sulfonylurea and su...

Claims

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Application Information

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IPC IPC(8): C07C309/86C07C303/02
Inventor 李映张建林牟庆平吴文雷姚刚侯晓峰成鲁南
Owner JINGBO AGROCHEM TECH CO LTD
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