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Method for preparing isobutylamido thiazolyl resorcinol

A technology based on thiazolyl resorcinol and isobutyramide, which is applied in the field of chemical synthesis, can solve the problems of unfriendly environment, many side reactions, and high cost, and achieve a simple synthesis process route, simple post-treatment, and few reaction steps Effect

Active Publication Date: 2020-11-17
泰州瑞仕诺医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the prior art has the following problems: 1. The price of 2,4-dihydroxyacetophenone is relatively expensive; 2. When methyl chloroacetate is used as a hydroxyl protecting group, the amount of methyl chloroacetate is relatively large and it is a highly toxic drug, which leads to an increase in cost; 3. Sulfur After the reaction of urea and isobutyryl chloride, the post-treatment is extremely inconvenient; the overall process steps are long and the cost is high. 4. When bromine is brominated at the alpha carbonyl position, it is highly toxic and corrosive, and the three wastes are difficult to handle and have many side reactions; 5. Deprotection requires a large amount of hydrochloric acid, and there is a lot of acidic wastewater, which is not environmentally friendly

Method used

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  • Method for preparing isobutylamido thiazolyl resorcinol
  • Method for preparing isobutylamido thiazolyl resorcinol

Examples

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Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of intermediate I

[0033] Weigh 2,220 grams of resorcinol, 2,100 grams of bromoacetic acid, and 5,500 mL of 48% boron trifluoride ether solution into a 10-liter reaction bottle, and slowly heat to 75°C (first heat to 65°C for 30 minutes, then heat up to 75°C °C to continue the reaction), the tail gas was absorbed with an aqueous solution of sodium hydroxide. After the reaction reaches 3 hours, trace the content of bromoacetic acid in the liquid phase. After it is less than 1%, cool to room temperature, slowly add 3000 ml of ice water dropwise, stir for 10 minutes, separate the liquid, dry the organic phase, and concentrate the organic phase to obtain about 2900 g of oil . The oil was separated by petroleum ether:ethyl acetate=50:1 column chromatography to obtain about 1800 g of off-white to light yellow solid with a purity of more than 98% and a yield of 51%.

Embodiment 2

[0034] Embodiment 2: the synthesis of intermediate II

[0035] Weigh 1,000 grams of isobutyryl chloride, 893 grams of thiourea, and 3 L of toluene, and add them to a 5-liter reaction bottle, reflux at 115°C for 3-4 hours, track the liquid phase, and absorb the tail gas with an aqueous solution of sodium hydroxide. Add 3 liters of water, distill the toluene, cool and crystallize. About 900 g of yellow crystalline solid was obtained by filtration, the purity was greater than 98%, and the yield was about 65%.

Embodiment 3

[0036] Embodiment 3: the synthesis of Thiamidol

[0037] Weigh 500 grams of Intermediate I, 333 grams of Intermediate II, 2.5 L of ethanol, and 285 grams of sodium bicarbonate, and add them to a 5-liter reaction bottle, and slowly raise the temperature to 80 ° C. After 30 minutes of reaction, follow the liquid phase, and the reaction is complete Finally, filter the inorganic salts, concentrate the organic matter, 1.5L ethyl acetate heat beating, and filter the product after cooling to obtain 530 grams of white to off-white solid with a purity greater than 99% and a yield of about 88%.

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Abstract

The invention discloses a method for preparing isobutylamido thiazolyl resorcinol. The method comprises the following steps: (1) reacting resorcinol with bromoacetic acid under the action of a catalyst to generate an intermediate shown as a formula I; (2) reacting thiourea with isobutyryl chloride to generate an intermediate shown as a formula II; and (3) reacting the intermediate shown in the formula I with the intermediate shown in the formula II under the action of alkali to generate isobutylamido thiazolyl resorcinol shown in a formula III. The synthesis steps provided by the invention aresimplified to three-step reaction, the process route is simple, the raw materials are easy to obtain, the reaction time is short, the post-treatment is simple and convenient, the purity is 99% or above, the total yield is 29.1% or above, the operation is simple, and the method is suitable for continuous industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing isobutyramide thiazolyl resorcinol. Background technique [0002] Thiamidol, also known as isobutyramide thiazolyl resorcinol, belongs to resorcinol derivatives, can effectively inhibit the production of tyrosinase, and can directly inhibit melanin from the source. It has been proven that its effective content of 0.2% can have obvious effects in the human body, and its key functions are: 1. Reduce the production of melanin; 2. Inhibit the transmission of pigment to keratinocytes. At present, the resorcinol series used in China are: 4-butylresorcinol, 4-hexylresorcinol, 4-phenylethylresorcinol, but 4-butylresorcinol, 4- Hexyl resorcinol has a low melting point and is easy to change color. In practical applications, the choice of addition amount will cause adverse reactions such as blackening and irritation. 4-Phenylethyl resorcinol has the disa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/46
CPCC07D277/46
Inventor 帅继山华晓光
Owner 泰州瑞仕诺医药科技有限公司
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