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Method for synthesizing 3-chloro-1,2-benzo iso thiazole compounds

A technology of benzisothiazole and benzisothiazoline, which is applied in the field of 3-chloro-1, can solve the problems of intractable phosphorus-containing wastewater, serious equipment corrosion, prominent environmental problems, etc., and achieves low production cost and no three wastes. , The effect of eliminating security risks

Inactive Publication Date: 2008-05-14
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The product obtained by the phosphorus oxychloride process contains a large amount of by-product polyphosphoric acid, which must be extracted with two kinds of organic solvents to obtain the product. Using phosphorus oxychloride as the chlorination reagent will seriously corrode the equipment, and the process also produces A large amount of phosphorus-containing wastewater is difficult to deal with, serious pollution problems, and prominent environmental problems
In production, there must be an additional set of equipment for producing and storing phosgene, and there are still great safety hazards in the process

Method used

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  • Method for synthesizing 3-chloro-1,2-benzo iso thiazole compounds
  • Method for synthesizing 3-chloro-1,2-benzo iso thiazole compounds
  • Method for synthesizing 3-chloro-1,2-benzo iso thiazole compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The amount ratio of feed material 1,2-benzisothiazolin-3-one: bis(trichloromethyl)carbonate:catalyst is 1:0.4:0.01,1,2-benzisothiazolin-3-one Feeding capacity is 151g (1mol), bis(trichloromethyl)carbonate charging capacity is 119g (0.4mol), organic solvent is chlorobenzene, catalyst is tetramethylguanidine, consumption is 1.2g (0.01mol).

[0025] In a 500mL four-necked flask equipped with a thermometer, a reflux condenser, a constant pressure dropping funnel, and mechanical stirring, 151g of 1,2-benzisothiazolin-3-one, bis(trichloromethyl)carbonate, Chlorobenzene 300ml and catalyst tetramethylguanidine. After the addition, heat up to 80-85°C, react for several hours, and monitor with TLC (developing solvent: ethyl acetate:petroleum ether=1:5). , Distilled at 10 mbar to obtain 147 g of pale yellow 3-chloro-1,2-benzisothiazole crystals, with a product yield of 86.7%, a purity of 98.0%, and a melting point of 40-41°C.

Embodiment 2

[0027] The amount ratio of feed material 1,2-benzisothiazolin-3-one:bis(trichloromethyl)carbonate:catalyst 1:0.4:0.01, 1,2-benzisothiazolin-3-one feed Amount is 151g (1mol), two (trichloromethyl) carbonate charging capacity is 119g (0.4mol), and organic solvent is chlorobenzene, and its consumption is 1,2-benzisothiazolin-3-ketone quality 3 times, the catalyst is tetramethylguanidine, and its consumption is 1.2g (0.01mol).

[0028] The reaction temperature was 110-115°C, and other operations were the same as in Example 1 to obtain 144g of light yellow 3-chloro-1,2-benzisothiazole crystals with a yield of 84.9%, a purity of 98.2%, and a melting point of 40-41°C.

Embodiment 3

[0030] The amount ratio of feed material 1,2-benzisothiazolin-3-one:bis(trichloromethyl)carbonate:catalyst 1:0.4:0.01, 1,2-benzisothiazolin-3-one feed Amount is 151g (1mol), and two (trichloromethyl) carbonate charging capacity is 119g (0.4mol), and organic solvent is dichlorobenzene, and its consumption is 1,2-benzisothiazolin-3-ketone quality 3 times, the catalyst is pyridine, and its consumption is 0.8g (0.01mol).

[0031] The reaction temperature was 125-130° C., and other operations were the same as in Example 1 to obtain 145 g of pale yellow 3-chloro-1,2-benzisothiazole crystals with a product yield of 85.5%, a purity of 98.2%, and a melting point of 40-41.

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Abstract

This invention relates to non substituent on N 3-chlorine-1,2-benzo isothiazole kind compound synthesis method, its formula is shown as (I). Material is 1,2-benzo isothiazoline-3-ketone and bi(tri chlorine methyl) carbonate, its formula is shown as formula (II), the compound said is prepared in organic solvent under organic amine catalyst function at 50-150 dgrees centigrade, R is hygrogen, halogen, nitryl, C1-C6 alkyl or alkoxy. Its technique route is advanced, technique condition is reasonable, phosphorus oxychloride and phosgene using is eliminated, so the problem of big safe hidden danger, heavy three waste pollutions are thoroughly eliminated, it has great application value and society economic benefit.

Description

(1) Technical field [0001] The invention relates to a synthesis method of 3-chloro-1,2-benzisothiazole compounds, in particular to a synthesis method using bis(trichloromethyl)carbonate as one of the raw materials. (2) Background technology [0002] 3-Chloro-1,2-benzisothiazole compounds are important intermediates for the preparation of pharmacologically active substances (see US5206366 and EP281309) and crop protection agents (DE-A1 2029387). [0003] Before the present invention was given, the chemical synthesis methods of 3-chloro-1,2-benzisothiazole compounds in the prior art mostly used cheap and easy-to-obtain 1,2-benzisothiazolin-3-ketones Compound and phosphorus oxychloride or phosgene chlorination prepared. As US 5,883,258 proposes to use 565g 1,2-benzisothiazolin-3-ketone and 400g phosgene to prepare 3-chloro-1,2-benzisothiazole compounds under the catalysis of tetramethylguanidine, in In US4590196, 1,2-benzisothiazolin-3-ketone and POCl 3 The mixture was heate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D275/04
Inventor 苏为科陈志卫楼芳彪徐园芬王博
Owner ZHEJIANG UNIV OF TECH