4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid
Dazoxiben
CAS: 78218-09-4
Molecular Formula: C₁₂H₁₃ClN₂O₃
4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid - Names and Identifiers
4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid - Physico-chemical Properties
| Molecular Formula | C₁₂H₁₃ClN₂O₃ |
| Molar Mass | 268.70 |
| Melting Point | 230-235°C |
| Solubility | DMSO : 62.5 mg/mL (232.60 mM; Need ultrasonic) |
| Storage Condition | 2-8°C |
| Physical and Chemical Properties | Chemical Properties Dazoxy Benzene Hydrochloride (Dazoxiben Hydrochloride):C12H12N2O3?HCl. [74226-22-5]. White crystals are obtained from ethanol and ether. Melting point 230~235 ℃, melting point 239~241 ℃. |
| Use | Uses selective inhibitors of TVA2 (thrombus A2) synthetase, selective inhibitors of thromboxane A2 synthetase. Used in the treatment of angina pectoris, and tried in the treatment of thromboembolic diseases, such as myocardial infarction and Raynaud's disease. |
| Target | Thromboxane (TX) synthase |
4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid - Upstream Downstream Industry
| Raw Materials | Acetic acid Potassium carbonate p-Toluenesulfonic acid 1,2-Dichloroethane Ethylparaben ETHYL 4-(2-CHLOROETHOXY)BENZOATE |
4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid - Reference
| Reference Show more | 1. Patrignani P , Filabozzi P , Catella F , et al. Differential effects of dazoxiben, a selective thromboxane-synthase inhibitor, on platelet and renal prostaglandin-endoperoxide metabolism.[J]. journal of pharmacology & experimental therapeutics, 1984, 228(2):472-477.2. Yu S M , Wu T S , Teng C M . Pharmacological characterization of cinnamophilin, a novel dual inhibitor of thromboxane synthase and thromboxane A2 receptor[J]. British Journal of Pharmacology, 1994, 111(3). |
4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 3.722 ml | 18.608 ml | 37.216 ml |
| 5 mM | 0.744 ml | 3.722 ml | 7.443 ml |
| 10 mM | 0.372 ml | 1.861 ml | 3.722 ml |
| 5 mM | 0.074 ml | 0.372 ml | 0.744 ml |
Last Update：2024-01-02 23:10:35
4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid - Production method
Method 1: Ethyl p-hydroxybenzoate, 50% sodium hydroxide, 1, 2-dichloroethane and TBOE, stirred at 60°C. Cold to room temperature, acidified with 2mol/L hydrochloric acid to a Ph value of about 2. The organic layer is divided, and the water layer is extracted with dichloroethane. Organic layers are combined, washed and dried. Concentrate, wash with ether, and dry to obtain compound (I) in 86% yield. Imidazole and 40% sodium hydroxide were stirred together until completely dissolved, dimethylformamide, compound (I) and TBOE were added, and stirred at 40 ℃. Steam out the solvent under reduced pressure and cool to room temperature. Add water to dissolve and acidify, and chloroform is extracted 3 times. The extracts are combined, washed with water and dried. Concentrated and recrystallized with glacial acetic acid to obtain dazoxybenzene hydrochloride with 78% yield and melting point 238-241 ℃.
Method 2: Ethyl p-hydroxybenzoate, p-toluenesulfonic acid (2-chloroethyl) ester, anhydrous potassium carbonate and butanone were stirred and refluxed. Concentrate and pour the residual liquid into the water while it is hot. The solid was filtered, washed with water until neutral, and recrystallized with ethanol to obtain ethyl 4-(2-chloroethoxy) benzoate with 85.7% yield.
4-(2-chloroethoxy) ethyl benzoate, imidazole, sodium hydroxide, phase transfer catalyst TEBA and dimethylformamide are mixed and stirred in the 9012. Add a proper amount of water and extract it with dichloromethane. The extract is concentrated, the residual liquid is added to sodium hydroxide solution for alkalization, and the reaction is carried out at 90 ℃. Acidification with concentrated hydrochloric acid, filtration precipitation, glacial acetic acid recrystallization. Dazolexobenzene hydrochloride. 51% yield.
Last Update：2024-04-10 22:29:15
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Raw Materials for 4-[2-(1H-lmidazol-1-yl)ethoxyl]benzoic acid
Acetic acid
Potassium carbonate
p-Toluenesulfonic acid
1,2-Dichloroethane
Ethylparaben
ETHYL 4-(2-CHLOROETHOXY)BENZOATE
Potassium carbonate
p-Toluenesulfonic acid
1,2-Dichloroethane
Ethylparaben
ETHYL 4-(2-CHLOROETHOXY)BENZOATE