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A kind of method for preparing isobutyryl 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 price, and achieve simple synthesis process route, convenient post-treatment, and short reaction time Effect

Active Publication Date: 2022-07-19
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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  • A kind of method for preparing isobutyryl thiazolyl resorcinol
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  • A kind of method for preparing isobutyryl thiazolyl resorcinol

Examples

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Effect test

Embodiment 1

[0032] Example 1: Synthesis of Intermediate I

[0033] Weigh 2220 grams of resorcinol, 2100 grams of bromoacetic acid, and 5500 mL of 48% boron trifluoride ether solution, respectively, and add them to a 10-liter reaction flask, and slowly heat to 75 ° C (first heat to 65 ° C for 30 min, then heat up to 75 ° C.) °C to continue the reaction), the tail gas is absorbed with an aqueous solution of sodium hydroxide. After the reaction reaches 3 hours, the content of bromoacetic acid is tracked in the liquid phase, and after less than 1%, cooled to room temperature, slowly added dropwise with 3000 ml of ice water, stirred for 10 minutes, liquid separation, dried organic phase, and concentrated organic phase to obtain about 2900 grams of oily matter . The oily substance was separated by petroleum ether:ethyl acetate=50:1 column chromatography to obtain about 1800 g of off-white to light yellow solid, the purity was more than 98%, and the yield was 51%.

Embodiment 2

[0034] Example 2: Synthesis of Intermediate II

[0035] Weigh 1,000 grams of isobutyryl chloride, 893 grams of thiourea, and 3 L of toluene, respectively, add them to a 5-liter reaction flask, perform a reflux reaction at 115°C for 3-4 hours, follow the liquid phase, and absorb the tail gas with an aqueous solution of sodium hydroxide. 3 liters of water was added, and after toluene was distilled, the mixture was cooled and crystallized. About 900 grams of yellow crystalline solid were obtained by filtration, the purity was more than 98%, and the yield was about 65%.

Embodiment 3

[0036] Example 3: 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, respectively, add them to a 5-liter reaction flask, and slowly heat up to 80 ° C. After 30 minutes of reaction, the liquid phase is tracked, and the reaction is completed. After that, filter the inorganic salt, concentrate the organic matter, 1.5L ethyl acetate hot slurry, after cooling, filter the product to obtain 530 grams of white to off-white solid, the purity is more than 99%, and the yield is about 88%.

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Abstract

The invention discloses a method for preparing isobutyrylamide thiazolyl resorcinol, comprising the following steps: (1) reacting resorcinol and bromoacetic acid under the action of a catalyst to generate an intermediate shown in formula I; ( 2) thiourea reacts with isobutyryl chloride to generate the intermediate shown in formula II; (3) the intermediate shown in formula I and the intermediate shown in formula II are reacted under the action of a base to generate isoform shown in formula III. Butanamidothiazolyl resorcinol. The synthesis steps provided by the invention are simplified to three-step reactions, the process route is simple, the raw materials are readily available, the reaction time is short, the post-processing is convenient, the purity is over 99%, the total yield is over 29.1%, the operation is simple, and it is suitable for continuous industrial production. .

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing isobutyryl thiazolyl resorcinol. Background technique [0002] Thiamidol, also known as isobutyrylamide thiazolyl resorcinol, is a derivative of resorcinol, which can effectively inhibit the production of tyrosinase, and can directly inhibit melanin from the root. It has been confirmed that its effective content of 0.2% can play a significant role in the human body, and its key functions: 1. Reduce the production of melanin; 2. Inhibit the transmission of pigment to keratinocytes. The resorcinol series currently used in China are: 4-butyl resorcinol, 4-hexyl resorcinol, 4-phenethyl resorcinol, but 4-butyl resorcinol, 4- Hexyl resorcinol has a low melting point and is easy to change color. In practical applications, due to the selection of the addition amount, it will lead to adverse reactions such as blackening and irritation. 4-Phenylethyl resorcinol has...

Claims

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Application Information

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Patent Type & Authority Patents(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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