Bisbenzothiazole disulfide and triphenylphosphine preparation by means of one pot

A technology for benzothiazole disulfide and triphenylphosphine, which is applied in the field of preparing dibenzothiazole disulfide and triphenylphosphine, can solve the problems of unsatisfactory methods, high reaction temperature, unfriendly environment, and the like, To achieve the effects of cheap reagents, high reaction yield and good product purity

Inactive Publication Date: 2009-02-04
ZHEJIANG UNIV OF TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The reduction method of triphenylphosphine oxide began to be studied and gradually increased from the reuse of spent catalysts, but the methods used were not satisfactory, either the cost was high, the operation was dangerous, and some reducing agents were more expensive, such as R 3 Al, NaAlH 4 +AlCl 3 , Cl 3 SiH, etc., or unfriendly to the environment, such as phosphorus method
Among them, the hydrogen peroxide oxidation method is relatively green, but the operation is cumbersome and the reaction temperature is relatively high.

Method used

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  • Bisbenzothiazole disulfide and triphenylphosphine preparation by means of one pot
  • Bisbenzothiazole disulfide and triphenylphosphine preparation by means of one pot
  • Bisbenzothiazole disulfide and triphenylphosphine preparation by means of one pot

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Feeding ratio is TPPO: BTC: M: organic base=1.0: 0.34: 2.0: 1.5, organic base is triethylamine, organic solvent A and B are chlorobenzene, organic solvent A in step (1) and step (2) The dosage of B and B is respectively 4 times and 2 times of TPPO feeding quality. The reaction temperature in the first stage is 20°C (T 1 ), reaction time 5h(t 1 ), the reaction temperature in the second stage is 20°C (T 2 ), reaction time 4h(t 2 ). The recrystallization solvent is isopropanol.

[0029] (1) Put chlorobenzene 111.2g, BTC (30.3g, 0.034mol), TPPO (27.8g, 0.1mol) into a 500mL four-necked flask equipped with a thermometer, dropping funnel, and mechanical stirring at 20°C, and keep warm for the reaction For 5 hours, the resulting reaction solution was directly used in step (2);

[0030] (2) At 20°C, add dropwise a mixed solution of chlorobenzene (55.6g) that is dissolved with M (33.4g, 0.2mol), triethylamine (15.2g, 0.15mol) in the reaction solution obtained in step (1), ...

Embodiment 2

[0033] Feeding ratio is TPPO: BTC: M: organic base=1.0: 0.4: 2.0: 2.0, organic base is pyridine, organic solvent A and B are toluene, organic solvent A and B in step (1) and step (2) The dosage is 3 times and 5 times of the mass of TPPO feeding respectively. T 1 =30°C, t 1 = 3h; T 2 =20°C, t 2 = 6h. The recrystallization solvent is isopropanol.

[0034] Others are the same as in Example 1, the product DM yield is 92.6%, HPLC purity 99.0%; TPP yield 91.0%, HPLC purity 98.8%.

Embodiment 3

[0036]Feeding ratio is TPPO: BTC: M: organic base=1.0: 0.34: 1.5: 1.5, organic base is triethylamine, organic solvent A is acetonitrile, and organic solvent B is chlorobenzene, in step (1) and step (2) The dosages of organic solvents A and B were 1 and 2 times the mass of TPPO feed, respectively. T 1 = 0°C, t 1 =10h;T 2 =90°C, t 1 = 2h. The recrystallization solvent is ethanol.

[0037] Others are the same as in Example 1, the product DM yield is 73.2%, and the HPLC purity is 99.3%; the TPP yield is 71.9%, and the HPLC purity is 98.3%.

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Abstract

The invention discloses a method for preparing bisbenzothiazole disulfide (DM) and triphenylphosphine (TPP) by a pot method, comprising the following processes: an organic solvent A, bis (trichloromethyl) carbonate shown in formula (II) and triphenyl phosphine oxide are sequentially added to a reaction bottle, and the insulating reaction is carried out for 0.5 to 10 hours at the temperature of minus 30 DEG C to 90 DEG C; the reaction solution is added with mixed solution of 2-sulfhydryl benzothiazole and organic base which are dissolved by an organic solvent B shown in formula (III), and the mixture reaction is carried out for 0.5 to 10 hours at the temperature of -30 DEG C to 90 DEG C; after the reaction is completed, drawing and filtering are carried out, the filter cake is dried and then the bisbenzothiazole disulfide is obtained, the organic solvent in the filter solution is recycled to obtain crude products, the crude products are re-crystallized to obtain the triphenylphosphine. The method has the advantages of simple operation, high reaction yield, high product purity and good atom economy, thus solving the problem that by-products can cause environment pollution, and the like, owning to difficult recovery and utilization in the process of producing cephalothin active ester, and the method has great implement value and potential social and economic benefits.

Description

(1) Technical field [0001] The present invention relates to a method for preparing dibenzothiazole disulfide (DM) and triphenylphosphine (TPP). (2) Background technology [0002] Cephalosporin active ester is the important intermediate of preparation cephalosporin, produces a large amount of waste liquids in the production cephalosporin active ester process, and its main component is 2-mercaptobenzothiazole (M) and triphenylphosphine oxide (TPPO), Due to the trouble and difficulty of post-processing, many enterprises transfer waste to other places or discharge it directly, resulting in serious environmental pollution. Research and development of by-product resource utilization technology to comprehensively utilize waste and turn waste into treasure can not only greatly reduce the discharge of waste, but also effectively reduce the production cost of cephalosporin active esters, which meets the requirements of green chemistry and has important social and social significance. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/78C07F9/52
Inventor 钟为慧吴登泽苏为科吴华悦顾士崇刘会军
Owner ZHEJIANG UNIV OF TECH
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