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Method for synthesizing p-acetamido benzene sulfonyl chloride by phosphorus pentachloride

A technology of acetaminophensulfonyl chloride and phosphorus pentachloride, which is applied in the field of preparation of sulfonamide drug intermediates, can solve the problems of increasing the cost of waste acid treatment, high dosage of chlorosulfonic acid, increasing production costs, etc., and achieve saving of repeated construction investment , high yield and prolong service life

Inactive Publication Date: 2013-08-14
CHONGQING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Another example is "A new method for the chlorosulfonation of acetanilide" in the 2nd issue of "Tianjin Chemical Industry" in 1990. The disclosed method 2---the thionyl chloride method, promptly selects thionyl chloride as the chlorination agent for the present There are synthetic methods to improve, although the highest yield can reach 90%, it can't fundamentally solve the problem of waste acid produced in the production process. At this time, in the production process, the consumption of chlorosulfonic acid is still relatively high, which increases production cost; and sulfur dioxide is added to the tail gas of the reaction, hydrogen chloride and sulfur dioxide are absorbed together when the tail gas is absorbed, and the two are difficult to separate, which increases the treatment cost of waste acid, thereby further increasing the production cost

Method used

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  • Method for synthesizing p-acetamido benzene sulfonyl chloride by phosphorus pentachloride

Examples

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Effect test

Embodiment 1

[0023] A kind of concrete steps of the method for synthesizing p-acetaminobenzenesulfonyl chloride with phosphorus pentachloride are as follows:

[0024] (1) Sulfonation reaction

[0025] With acetanilide and chlorosulfonic acid as raw materials, the chlorosulfonic acid is first diluted, that is, the volume ratio of chlorosulfonic acid: chloroform organic solvent is 1: 1.1, the chlorosulfonic acid and the chlorosulfonic organic solvent are placed in the container, Stir and mix evenly to prepare a chlorosulfonic acid dilution. Then by acetanilide: the chlorosulfonic acid mol ratio in the chlorosulfonic acid dilution is the ratio of 1: 2.95, in the chlorosulfonic acid dilution, at a temperature of 14°C, add acetanilide (99% purity). After the addition of acetanilide was completed, the mixture was stirred at low temperature for 30 minutes. Then, the temperature was raised to 59° C. while stirring, and the sulfonation reaction was carried out with heat preservation for 60 minut...

Embodiment 2

[0031] A kind of concrete steps of the method for synthesizing p-acetaminobenzenesulfonyl chloride with phosphorus pentachloride are as follows:

[0032] In the (1) step, chlorosulfonic acid: the volume ratio of chloroform organic solvent is 1: 1.0, and acetanilide: the chlorosulfonic acid mol ratio in the chlorosulfonic acid diluent is 1: 2.50, at 12 ℃, in 5 batches Add acetanilide while stirring, continue to stir for 25 minutes, then raise the temperature to 59°C while stirring, and keep it warm for 60 minutes, according to the molar ratio of sulfonated liquid: ammonium chloride desiccant is 1:0.018, stir for 10 minutes;

[0033] In the (2) step, sulfonated oil: the volume ratio of chloroform organic solvent is 1: 0.8, and the acetanilide consumed in the sulfonated oil diluent: the mol ratio of phosphorus pentachloride chlorinating agent is 1: 0.92, stirs Heat up to 59°C, and keep warm for chlorination reaction for 150 minutes;

[0034] In the (3) step, the p-acetamidobenzene...

Embodiment 3

[0036] A kind of concrete steps of the method for synthesizing p-acetaminobenzenesulfonyl chloride with phosphorus pentachloride are as follows:

[0037] In the (1) step, chlorosulfonic acid: the volume ratio of carbon tetrachloride organic solvent is 1: 1.1, and acetanilide: the chlorosulfonic acid mol ratio in the chlorosulfonic acid dilution is 1: 2.00, at 15 ℃, Add acetanilide in 5 batches while stirring, continue to stir for 32 minutes, then raise the temperature to 54°C while stirring, and keep it warm for 65 minutes, according to the molar ratio of sulfonated liquid: ammonium chloride desiccant is 1:0.011, stir for 10 minutes ;

[0038] In the (2) step, sulfonated oil: the volume ratio of chloroform organic solvent is 1: 0.7, and the acetanilide consumed in the sulfonated oil diluent: the mol ratio of phosphorus pentachloride chlorinating agent is 1: 1.39, stirs Heat up to 66°C, and keep warm for chlorination reaction for 180 minutes;

[0039] In the (3) step, the p-a...

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Abstract

The invention relates to a method for synthesizing p-acetamido benzene sulfonyl chloride by phosphorus pentachloride, relating to the preparation method for sterilization and mould inhibition midbody of sulfonamides. The invention takes acetanilide and chlorosulfonic acid as raw materials, uses phosphorus pentachloride as chlorinating agent; under the action of organic dissolvent, the raw materials are sulfonated, chloridized, separated, and washed to obtain the product. The invention has the effects of little chlorosulfonic acid usage, high product yield, few generated waste acid,, completely cycling dissolvent, recycled by-products, low manufacturing cost, being convenient to popularize and apply, and the like. The products prepared by the method can be widely applied to the preparation of the sterilization and mould inhibition of sulfonamides and industries such as coating, plastics, pesticides, etc.

Description

technical field [0001] The invention belongs to the technical field of preparation of sulfonamide drug intermediates, in particular to a preparation method of bactericidal and enzyme-inhibiting drug intermediates of sulfonamide drugs. Background technique [0002] At present, the mainstream pillar of the pharmaceutical industry is developing in a diversified direction. However, the status of sulfa drugs is unshakable. As an important intermediate of sulfonamides, p-acetamidobenzenesulfonyl chloride can be widely used in the preparation of sulfonamides, such as sulfathiazole, sulfisoxazole, sulfamethoxazole, sulfapyridine, sulfamethoxazole Dimethylisopyrimidine, etc., its economic value and social utility are huge. In addition, p-acetamidobenzenesulfonyl chloride can also be used in coatings, plastics and other fields. Therefore, the synthesis of p-acetaminobenzenesulfonyl chloride is an important step in the preparation of sulfonamides. In order to maximize the productio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/88C07C303/08
Inventor 魏顺安罗自萍谭世语阳杨邹晶董立春张红晶刘子林
Owner CHONGQING UNIV
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