In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride, other downstream synthetic routes, hurry up and to see.
Related Products of 72830-09-2 ,Some common heterocyclic compound, 72830-09-2, molecular formula is C8H11Cl2NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 1: Preparation of Pantoprazole sodium compound of formula-la:Added a solution of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (50 grams in 250ml of water) to a solution of 49.8 grams of 5-difluoromethoxy 2-mercaptobenzimidazole, 500 ml water and sodium hydroxide (22.5 grams of flakes in 27.5 ml of water), slowly at 25-35C. Stirred the reaction mixture for 3 hours. Extracted the reaction mixture thrice with methylene chloride. Separated the organic and aqueous layer. Washed the organic layer with water. Cooled the organic layer to -5 to 0C. Added 550 grams of 3.1% sodium hypochlorite solution having pH 8.75 and assay 3.2 to the above reaction mixture at -5 to 0C. Stirred the reaction mixture for 3 hours at -5 to 0C. Quenched the reaction mixture with 56 grams of ammonium sulphate at below 10C. Stirred the reaction mixture for 30 minutes. Separated the organic and aqueous phases. Extracted the aqueous phase twice with methylene chloride. Washed the organic layer with water. Dried the organic phase over sodium sulphate. Distilled the solvent completely under reduced pressure at below 45C. Added 37.5 ml of acetone to the above crude and distilled the solvent completely under reduced pressure at below 45C. Dissolved the residue in 375 ml of acetone at 25-35C. Heated the reaction mixture to reflux temperature. Stirred the reaction mixture for 30 minutes at reflux temperature. Cooled the reaction mixture to 18-23C. Added aqueous sodium hydroxide solution (8.5 grams in 10 ml of water) at 18-23C. Stirred the reaction mixture for 1 hour at 18-23C. Cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 3 hours. Filtered the solid and washed with acetone followed by washed with methylene chloride. The obtained solid is purified in acetone to get pure compound.The amount of sulfone compound of formula-6 and compound of formula- 1 present in the obtained solid was measured using HPLC and the results are as follows. Yield: 65 grams Example-3: Preparation of pantoprazole sodium sesquihydrate compound of formula-la:Added a solution of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (50 grams in 250ml of water) to a solution of 49.8 grams of 5-difluoromethoxy-2- mercaptobenzimidazole, 500 ml of water and aqueous sodium hydroxide (22.5 grams of flakes in 27.5ml of water), slowly at 25-350C. Stirred the reaction mixture for 3 hours. Extracted the reaction mixture thrice with methylene chloride. Separated the organic and aqueous layer. Washed the organic layer with water. Added 550 grams of 3.1% sodium hypochlorite having pH 8.75 and assay 3.2 to the above reaction mixture at 25-300C for 2 hours. Stirred the reaction mixture for 10 hours at 25-3O0C. Quenched the reaction mixture with water at 25-300C. Stirred the reaction mixture for 30 minutes at 25-300C. Separated the organic and aqueous phases. Extracted the aqueous layer with methylene chloride. Washed the organic phase twice with aqueous sodium hydroxide solution. Separated the phases. Cooled the aqueous layer to 10-150C. Adjusted the pH of the reaction mixture to 9.3 with aqueous acetic acid. Added 250 ml of methylene chloride. Stirred the reaction mixture for 15 minutes. Separated the organic phase. Extracted the reaction mixture with methylene chloride. Washed the organic layer with water. Distilled the solvent completely from organic layer at below 45C under reduced pressure. Added 37.5 ml of acetone to the crude and distilled the solvent completely under reduced pressure at below 45C. Dissolved the residue in 375 ml of acetone at 25-35C. Heated the reaction mixture to reflux temperature. Stirred the reaction mixture for 30 minutes at reflux temperature. Cooled the reaction mixture to 18-23C. Added aqueous sodium hydroxide solution (8.5 grams in 10 ml of water) at 18-23C. Stirred the reaction mixture for 1 hour at 18-23C. Cooled the reaction mixture to 0-50C and 35 ml of methylene chloride was added. Stirred the reaction mixture for 3 hours. Filtered the solid and washed with methylene chloride. The above obtained compound can optionally purified as follows.Acetone (400 ml) was added to the above obtained wet compound and heated to reflux. The obtained solution was treated with carbon and cooled the filtrate to 0-5C. Stirred for 2 hours. Filtered the precipitated solid and washed with 30 ml of chilled acetone followed by washing with 50 ml of methylene chloride. Methylene chloride (250 ml) was added to the obtained wet compound at 25-35C. Stirred the reaction mixture for 90 minutes at 25-350C. Filtered the precipitated solid and washed with 25 ml of methylene chloride. Dried the compound at 40-500C for 10 hours.Yield: 70 grams W.C : 5.9 %HPLC : 99.93 %; 0.02 % (Sulfone Impurity) PSD : before micronization : D (v, 0.1) is 0.4 mum ; D (v, 0.5) is 8.73 mum; D (v, 0.9) is 27.7 mum andD(4,3) is 12.02 mum.PSD : after micronization ๐ (v,0.1) is 1.75 mum; D (v,Q.5) is 4.92 mum; D (v,0.9) is 13.10 mum andD(4,3) is 6.35 mum.Exam…
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; MSN LABORATORIES LIMITED; WO2008/1392; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem