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Method for synthesizing 3-methyl-2-benzothiazolinone hydrazone hydrochloride and its hydrate

A kind of technology of benzothiazolinone hydrazone hydrochloride and benzothiazolinone hydrazone, which is applied in the synthesis field of 3-methyl-2-benzothiazolinone hydrazone hydrochloride and its hydrate, and can solve the cost Expensive, troublesome operation and other problems, to achieve the effect of low cost, convenient operation and short synthesis route

Active Publication Date: 2018-12-18
青岛贞开生物医药技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there are also disadvantages such as troublesome operation and high cost

Method used

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  • Method for synthesizing 3-methyl-2-benzothiazolinone hydrazone hydrochloride and its hydrate
  • Method for synthesizing 3-methyl-2-benzothiazolinone hydrazone hydrochloride and its hydrate
  • Method for synthesizing 3-methyl-2-benzothiazolinone hydrazone hydrochloride and its hydrate

Examples

Experimental program
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Effect test

Embodiment 1

[0026] (1) N-Methylaniline (0.1mol, 10.7g), triethylamine (0.11mol, 11g), carbon disulfide (0.1mol, 7.6g) were dissolved in 100mL of methanol, and stirred at 0°C for two hours, and then continue to react at room temperature for two hours. After the reaction is complete, the methanol solvent is spun off, 100mL of ethyl acetate is added, washed twice with water, dried over anhydrous sodium sulfate, and then the ethyl acetate is spun off and washed with methyl tert-butyl 15 g of N-methyl-N-phenyldithiocarbamate was obtained by crystallization of base ether, with a yield of 82%. HNMR (DMSO-d 6 ): δppm=7.29(d,2H),7.17(m,3H),3.66(s,3H).

[0027] (2) Dissolve the compound N-methyl-N-phenyldithiocarbamate (0.1mol, 18.3 grams) obtained in step (1) in 200mL of dichloromethane, add bromine (0.1 mol, 16 grams) for reaction, about half an hour dropwise, and then stirred for 2 hours, the reaction was completed, washed twice with water, the organic layer was dried with anhydrous sodium sul...

Embodiment 2

[0032] (1) N-methylaniline (0.1mol, 10.7g), triethylamine (0.12mol, 12g), carbon disulfide (0.1mol, 7.6g) were dissolved in 110mL of ethanol, and stirred at 0°C for two hour, and then continue to react for two hours at room temperature. After the reaction is completed, the ethanol solvent is spun off, 120 mL of ethyl acetate is added, washed twice with water, dried over anhydrous sodium sulfate, and then rotary evaporated to remove ethyl acetate to obtain a crude product. Then crystallize with methyl tert-butyl ether to obtain 15.2 g of N-methyl-N-phenyldithiocarbamate, with a yield of 83%.

[0033] (2) The compound N-methyl-N-phenyldithiocarbamate (0.1mol, 18.3 grams) obtained in step (1) was dissolved in 200 mL of chloroform, and bromine (0.11 mol, 17.6 g) to react, about half an hour to complete the dropwise addition, and then stir the reaction for 2 hours, the reaction was completed, washed twice with water, the organic layer was dried with anhydrous sodium sulfate, concen...

Embodiment 3

[0038] (1) N-methylaniline (0.1mol, 10.7g), triethylamine (0.13mol, 13g), carbon disulfide (0.11mol, 8.4g) were dissolved in 120mL of methanol, and stirred at 0°C for two hour, and then continue to react at room temperature for two hours. After the reaction is completed, the methanol solvent is spun off, and 120 mL of ethyl acetate is added to dissolve, then washed twice with water, dried over anhydrous sodium sulfate, and the ethyl acetate is spun off to obtain the crude product , crystallized with methyl tert-butyl ether to obtain 15.5 g of N-methyl-N-phenyldithiocarbamate, with a yield of 85%.

[0039] (2) The compound N-methyl-N-phenyldithiocarbamate (0.1mol, 18.3 grams) obtained in step (1) was dissolved in 220mL of dichloromethane, and bromine (0.12 mol, 19.2 grams) to react, about half an hour dropwise, and then stirred for 2 hours, the reaction was completed, first washed with sodium bicarbonate solution, then washed once with water, the organic layer was dried with an...

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Abstract

The invention provides a method for synthesizing 3-methyl-2-benzothiazolinone hydrazone hydrochloride and its hydrate, and belongs to the field of organic synthesis. The method comprises the followingsteps: reacting N-methylaniline with carbon disulfide to obtain N-methyl-N-phenyldithiocarbamic acid, reacting the N-methyl-N-phenyldithiocarbamic acid with bromine to obtain 3-methylbenzothiazole-2-thione, reacting the 3-methylbenzothiazole-2-thione with hydrazine hydrate to generate 3-methyl-2-benzothiazolinone hydrazone, reacting the 3-methyl-2-benzothiazolinone hydrazone with hydrochloric acid to obtain 3-methyl-2-benzothiazolinone hydrazone hydrochloride, and re-crystallizing the 3-methyl-2-benzothiazolinone hydrazone hydrochloride in water to obtain the 3-methyl-2-benzothiazolinone hydrazone hydrochloride hydrate. The method has the advantages of cheap and easily available raw materials, simple operation process and potential industrial amplified application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a synthesis method of 3-methyl-2-benzothiazolinone hydrazone hydrochloride and a hydrate thereof. technical background [0002] 3-Methyl-2-benzothiazolinone hydrazone hydrochloride, CAS: 149022-15-1, molecular formula: C8H10ClN3S, molecular weight: 215.7. 3-methyl-2-benzothiazolinone hydrazone hydrochloride hydrate , CAS: 38894-11-0, molecular formula: C8H12ClN3OS, molecular weight: 233.7, and its structural formulas are as follows: [0003] [0004] 3-Methyl-2-benzothiazolinone hydrazone hydrochloride and its hydrate can be used in the photometric determination of fatty aldehydes, the determination of hexosamines in mucopolysaccharides, and the photometric determination of trace selenium in environmental samples. Among them, the determination of fatty aldehydes, especially formaldehyde, is of great significance. For example, the decoration materials used in newly...

Claims

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Application Information

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IPC IPC(8): C07D277/82
CPCC07D277/82
Inventor 余书强
Owner 青岛贞开生物医药技术有限公司
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