Synthesis method of 4-bromo-2-methoxybenzenesulfonyl chloride
A technology of methoxybenzenesulfonyl chloride and a synthesis method, which is applied in the field of preparation of pharmaceutical synthesis intermediates, can solve the problems of short reaction time, high requirements on reaction conditions, difficult purification and the like, and is suitable for large-scale production and preparation technology. Simple, easy-to-use ingredients
Inactive Publication Date: 2020-08-25
上海毕得医药科技股份有限公司
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Problems solved by technology
[0005] In this method, the yield is low, only 5%. Because chlorosulfonic acid needs to be used, and the reaction conditions are very demanding, and the reaction time is relatively short, it is not easy to control.
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Embodiment 1
[0030] Embodiment 1: Preparation of 4-bromo-2-methoxybenzenesulfonyl chloride
[0031]
[0032] According to the above reaction route as shown in the formula, add 0.5g0.014eq of cuprous chloride to 750ml of water, add 198.8g4.5eq of thionyl chloride dropwise at 0-10°C, and keep it at room temperature for 24 hours to form a spare solution A for use ;
[0033] Add 1eq75g of compound 1 to 375ml of acetic acid at minus 0-10°C, then dissolve 1.1eq of 28.18g sodium nitrite in 118ml of water and drop it into the system, keep it at -5°C-0°C for 1 hour, and prepare for use Solution B;
[0034] Then, under the temperature control condition of 0°~10°, slowly drop the prepared spare solution B into the spare solution A, then raise it to room temperature 25°C, react for 24 hours, spot the plate to detect the raw materials after the reaction is complete, rinse the ice Extracted with water and DCM, backwashed with saturated aqueous sodium chloride solution, dried over anhydrous sodium s...
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The invention relates to a synthesis method of 4-bromo-2-methoxybenzenesulfonyl chloride. The synthesis method comprises the following steps of: adding cuprous chloride into water, dropwise adding thionyl chloride at 0-10 DEG C, and reacting at room temperature for 16-24 hours to form a standby solution A; adding 4-bromine-2-methoxyaniline into an acidic solvent at 0-10 DEG C, dropwise adding a sodium nitrite solution into the 4-bromine-2-methoxyaniline acidic solution system under the condition of controlling the temperature at 0-10 DEG C, and reacting for 30 minutes to 1 hour while keeping the temperature at -5 DEG C to 0 DEG C to form a standby solution B; finally, slowly dropwise adding the standby solution B into the standby solution A under the condition of controlling the temperature at 0-10 DEG C, enable the standby solution B and the standby solution A to be fully mixed and react, then raising the temperature to the room temperature of 25 DEG C, reacting for 8-24 hours, then introducing ice water, performing DCM extraction, backwashing, drying and spin-drying, and then performing purifying to obtain the compound 4-bromo-2-methoxybenzenesulfonyl chloride.
Description
technical field [0001] The invention belongs to the technical field of preparation of pharmaceutical synthesis intermediates, and relates to a synthesis method of 4-bromo-2-methoxybenzenesulfonyl chloride. The obtained 4-bromo-2-methoxybenzenesulfonyl chloride is used in the preparation of growth hormone secretion ( GHS) receptor partial or total agonist drug use. Background technique [0002] The growth hormone secretagogue (GHS) receptor is a growth-promoting factor (Chrelin) and growth hormone secretagogue receptor (CHS) receptor, and its gene is located in the 26.31 region of the long arm of human chromosome 3. The content of GHSR is highest in the central nervous system and the anterior pituitary, and now it is found that CHSR is also in the hypothalamus (anterior hypothalamus, anterolateral nucleus of hypothalamus, ventromedial nucleus of hypothalamus, anterior ventral preoptic nucleus, suprachiasmatic nucleus , supraoptic nucleus, arcuate nucleus, paraventricular nuc...
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IPC IPC(8): C07C309/87C07C303/02
CPCC07C303/02C07C309/87
Inventor 郦荣浩周永加
Owner 上海毕得医药科技股份有限公司