The synthetic method of bithiazole quaternary ammonium salt

A synthesis method and quaternary ammonium salt technology, applied in the direction of organic chemistry and the like, can solve the problems of complex product components, unable to obtain expected products, difficult to obtain high-purity products, etc., achieving broad application prospects and easy large-scale industrial production and application , the effect of easy operation

Inactive Publication Date: 2015-11-25
SHANGHAI LUGUAN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] In a word, the expected products cannot be obtained by known patents or methods reported in the literature, and the product components are complex, so it is difficult to obtain high-purity products

Method used

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  • The synthetic method of bithiazole quaternary ammonium salt
  • The synthetic method of bithiazole quaternary ammonium salt
  • The synthetic method of bithiazole quaternary ammonium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of 3,4-Dimethyl-2-heptylthiothiazol-3-ium Iodide Salt

[0040]

[0041] Add 3,4-dimethylthiazole-2(3H)-thioketone (reference: ActaChemicaScandinavica, 1999, 53(10), 861–866) (2.42g, 16.8mmol) and iodine in a single-necked bottle Substituting n-heptane (3.8g, 16.8mmol), heated to 120°C for 1h under the protection of nitrogen and reacted for 1h, a red viscous substance was formed, cooled, added ethanol and stirred quickly, a large amount of yellow solid was formed, filtered to obtain 3.66g, product The rate is 58.7%.

[0042] h 1 NMR (400MHz, d 6 -DMSO): δH7.84(s, 1H), 3.79(s, 3H), 3.47(t, 2H, J=7.2Hz), 2.47(s, 3H, CH 3 ), 1.76-1.83(m, 2H), 1.39-1.46(m, 2H), 1.27-1.35(m, 6H), 0.85(t, 3H, J=6.8Hz) (see figure 1 )

[0043] LC-MS: M + =244.0

Embodiment 2

[0045] Synthesis of 2,4-Dimethyl-3-heptylthiazol-3-ium Iodide Salt

[0046]

[0047]Add 2,4-dimethylthiazole (21.5g, 0.19mmol), iodoheptane (81.2g, 0.57mmol) and 200ml of toluene into a single-necked bottle, heat to 120°C under nitrogen protection and reflux for 2 hours, cool , The precipitated solid was washed with ethanol to obtain 46.0 g of white solid with a yield of 71.4%.

[0048] h 1 NMR (400MHz, d 6 -DMSO): δ7.79(s, 1H), 4.29(t, 2H, J=8.0Hz), 2.97(s, 3H, CH 3 ),2.53(s,3H,CH 3 ), 1.67-1.73(m, 2H), 1.327-1.33(m, 8H), 0.86(t, 3H, J=6.8Hz) (see figure 2 )

[0049] LC-MS: M + =212.1

Embodiment 3

[0051] Synthesis of 2,4-Dimethyl-3-heptylthiazol-3-ium Iodide Salt

[0052] Put a magnet in a 250ml single-mouth bottle, add 2,4-dimethylthiazole (1.7g, 15mmol), iodo-n-heptane (8.48g, 37.5mmol), under nitrogen protection conditions, at 130°C Reaction, reacted for 16 hours, the reaction liquid was separated, and the lower layer was a black oil. After cooling, it was fully stirred or ultrasonicated, and a large amount of solids were produced. Adding ethanol, ultrasonicated or stirred to fully disperse the solid matter, and suction filtered to obtain 3.82 g of white solids, with a yield of 75.0%. .

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Abstract

The invention provides a synthesis method of a dithiazole quaternary ammonium salt, which comprises the following steps of: when R is equal to R', step one, adding iodo n-heptane in 2,4-dimethylthiazole for reaction to obtain 2,4-dimethyl-3-heptyl thiazole-3-onium iodo salt, step two, carrying out reaction on 4-methylthiazole-2-mercaptan and iodo n-heptane to obtain a product 3-heptyl-4-methylthiazole-2(3H)-sulfoketone, step three, carrying out reaction on the product in the step two and iodo n-heptane to obtain an intermediate 3-heptyl-2-heptyl sulfenyl-4-methylthiazole-3-onium iodo salt, and step four, carrying out reaction on the products in the steps three and one in the presence of organic alkali to obtain yellow dithiazole quaternary ammonium salt; and when R is not equal to R', replacing the alkyl substituent group R' on N in the step two by R' different from the step one. According to the synthesis method, the generation of by-products is avoided, the final product is easy to separate, and the purity and the yield are high, so that the synthesis method is easy for large-scale industrial production and application.

Description

technical field [0001] The invention relates to a method for synthesizing components of skin care products, in particular to a method for synthesizing bithiazole quaternary ammonium salt. Background technique [0002] Thiazole quaternary ammonium salts have excellent antistatic, bactericidal and antiseptic capabilities, and can be used as antistatic agents and softeners in textiles, oil production, fibers, leather and other fields; Piaoning can be used for the treatment of acne, acne, etc. , has an important application in the field of cosmetics, as a conditioner, bactericide, whitening agent, etc. It is widely used in personal care products such as shampoo, facial products, and body cream; as a pharmaceutical ingredient, this product is used in the pharmaceutical industry to treat acne Acne and dermatitis etc. [0003] Up to now, there are few reports on the synthetic case literature of bithiazole quaternary ammonium salt. Journal of the Scientific Research Institute, Toky...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/22
CPCC07D277/22
Inventor 苏东亮
Owner SHANGHAI LUGUAN BIOTECH
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