5-(2-sulfanylidene-3H-1,3-thiazol-4-yl)thiophene-2-carboxamide
MCT
CAS: 52560-89-1
Molecular Formula: C8H6N2OS3
5-(2-sulfanylidene-3H-1,3-thiazol-4-yl)thiophene-2-carboxamide - Names and Identifiers
5-(2-sulfanylidene-3H-1,3-thiazol-4-yl)thiophene-2-carboxamide - Physico-chemical Properties
| Molecular Formula | C8H6N2OS3 |
| Molar Mass | 242.34 |
| Density | 1.63 |
| Melting Point | >236oC (dec.) |
| Boling Point | 471.1±55.0 °C(Predicted) |
| Flash Point | 238.7°C |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | 4.8E-09mmHg at 25°C |
| Appearance | Solid |
| Color | Pale Yellow |
| pKa | 7.23±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.806 |
5-(2-sulfanylidene-3H-1,3-thiazol-4-yl)thiophene-2-carboxamide - Reference Information
| Use | 2-formamido-5-(2-mercapto-1, 3-thiazol-4-yl)-thiophene is 5-(2-mercapto-4-thiazolyl) thiophene-2-formamide is an intermediate of arolol hydrochloride. Arotinolol hydrochloride is a selective β1-adrenoceptor antagonist, which is mainly used in the treatment of mild to moderate essential hypertension, angina pectoris, rapid arrhythmia and primary tremor. While choosing to inhibit β-adrenoceptors, it has a slight blocking effect on α1-adrenoceptors, thereby reducing sympathetic nerve tension, making the antihypertensive effect more ideal. Arotinolol hydrochloride was developed by Sumitomo Pharmaceutical Co., Ltd., and was first listed in Japan in 1985. |
| application | preparation of arotinolol hydrochloride (compound of structural formula I) 63.00g(0.86mol) of tert-butylamine and 39.51g(0.17mol) of triethylbenzyl ammonium chloride were added to 350ml of anhydrous methanol. When the temperature is raised to 65~70 ℃, the methanol solution of epichlorohydrin (401.21g(4.34mol) epichlorohydrin dissolved in 700ml anhydrous methanol) is slowly added dropwise to the above system. After dropping, keep warm and react for 5 hours. After the reaction is completed, it is concentrated under reduced pressure. In the residue, 83.36g(0.344mol), 131.30g(0.95mol) potassium carbonate and 28.55g(0.172mol) potassium iodide of the compound of structural formula IV were added in sequence, and the temperature was raised to 70~75 ℃ for heat preservation reaction. After the reaction is completed, the temperature is reduced to 0~10 ℃, 300ml of water and 600ml of dichloromethane are added to the above system in turn, and the liquid is separated by standing. The water layer is discarded, and the organic phase is dried by adding 80.00g of anhydrous sodium sulfate. Filtration, the filtrate is concentrated under reduced pressure, 30ml of concentrated hydrochloric acid (12N) is added to the residue, and stirred to dissolve. Concentrate under reduced pressure, add 240ml ethyl acetate and 75ml anhydrous methanol to the residue, and stir for crystallization. Filtration, filter cake drying at 60 ℃ to obtain target compound (14.73g, yellow solid), yield: 10.50%. |
Last Update：2024-04-10 22:29:15
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