New process synthesis method for 2-sulfydryl-5-methoxybenzimidazole

A technology for the synthesis of methoxybenzimidazole and its synthesis method, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of unfavorable green and environmental protection industrial production, operators and environmental hazards, poor operation safety, etc., and achieve the optimization and improvement of the process synthesis route method, Effect of improving drug safety and reducing preparation cost

Inactive Publication Date: 2019-06-14
成都泰蓉生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing public preparation method uses nitrification reaction, which has a high risk factor and poor operation safety, which improves the safety level of production and production cost, which is not conducive to the promotion and application of industrialization; it is harmful to operators and the environment, and the cost of energy consumption is high. Produce a large amount of polluting sewage, which is not conducive to green and environmentally friendly industrial production

Method used

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  • New process synthesis method for 2-sulfydryl-5-methoxybenzimidazole
  • New process synthesis method for 2-sulfydryl-5-methoxybenzimidazole
  • New process synthesis method for 2-sulfydryl-5-methoxybenzimidazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097]

[0098] 1) Put 8.8 g of potassium carbonate and 150 mL of DMF into the reaction flask, add 5.0 g of compound A-1 and 13.5 g of methyl iodide, and heat to 40° C. and stir for 18 hours. The reaction liquid was cooled, filtered with suction, washed with water, dried, and concentrated to obtain compound A-2 (4.8 g, yield 89%);

[0099] 2) Add 0.5 g of compound A-2 and 5.2 mL of DMF to the reaction flask, add 0.8 g of potassium carbonate and 0.3 g of benzylamine in turn, the reaction solution is heated to 80°C and stirred for 4 hours, filtered, concentrated under reduced pressure to remove the solvent, washed with water, and dried Obtain compound A-3 (0.73 g, yield 97%);

[0100] 3) Add 0.3 g of compound A-3 and 10 mL of methanol into the reaction flask, add 0.06 g of 10% palladium on carbon, replace the hydrogen with the reaction solution at 30°C, stir for 20 hours, filter, and concentrate under reduced pressure to remove the solvent to obtain compound A-4 (0.16g , The yield i...

Embodiment 2

[0103]

[0104] 1) The compound A-2 was obtained by the operation similar to step 1 of Example 1;

[0105] 2) Add 0.5 g of compound A-2 and 3 mL of DMF to the reaction flask, add 0.4 g of cesium carbonate and 0.6 g of benzylamine in turn, the reaction solution is heated to 100°C and stirred for 2 hours, filtered, concentrated under reduced pressure to remove the solvent, washed with water, and dried to obtain Compound A-3 (0.7g, yield 95%);

[0106] 3) Add 0.3g of compound A-3 and 9mL of methanol into the reaction flask, add 0.03g of 5% palladium on carbon, replace the hydrogen with the reaction solution at 60°C, stir for 12h, filter, concentrate under reduced pressure to remove the solvent to obtain compound A-4 (0.14g , The yield is 96%);

[0107] 4) Add 0.1 g of compound A-4, 0.04 g of potassium hydroxide, 0.07 g of carbon disulfide and 10 mL of ethanol into the reaction flask. The reaction solution was heated to 60°C and stirred for 14 hours, a small amount of activated carbon w...

Embodiment 3

[0109]

[0110] 1) The compound A-2 was obtained by the operation similar to step 1 of Example 1;

[0111] 2) Add 0.5 g of compound A-2 and 10 mL of DMF to the reaction flask, add 1.6 g of potassium hydroxide and 0.45 g of benzylamine in turn, the reaction solution is heated to 120°C and stirred for 8 hours, filtered, concentrated under reduced pressure to remove the solvent, washed with water, and dried Obtain compound A-3 (0.75g, yield 98%);

[0112] 3) Add 0.3g of compound A-3 and 12mL of methanol into the reaction flask, add 0.09g of zinc powder, the reaction solution replaces hydrogen at 20°C and stirred for 48h, filtered, and concentrated under reduced pressure to remove the solvent to obtain compound A-4 (0.12g, yield 95%);

[0113] 4) Add 0.1 g of compound A-4, 0.075 g of potassium hydroxide, 0.07 g of carbon disulfide and 30 mL of ethanol into the reaction flask, the reaction solution was heated to 70°C and stirred for 4 hours, a small amount of activated carbon was added, ...

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Abstract

The invention discloses a new process synthesis method for 2-sulfydryl-5-methoxybenzimidazole. The new process synthesis method comprises the following steps: preparing N-benzyl-5-methoxy-2-nitroaniline through substitution reaction of 2-fluorine-4-methoxy-1-nitrobenzene and benzylamine; triggering hydrogenation reduction reaction, thereby acquiring 4-metoxybenzene-1,2-diamido; triggering cyclization reaction, thereby acquiring a target product compound 2-sulfydryl-5-methoxybenzimidazole. According to the new process synthesis method for 2-sulfydryl-5-methoxybenzimidazole provided by the invention, the synthetic route method is optimized and improved, operation danger level and production cost are reduced, operation safety is high, aftertreatment is green and environment-friendly, steps and processes are simple, solvent and technological conditions are safe and low-cost, environment-friendly industrial production can be realized and application prospect is bright.

Description

Technical field [0001] The invention relates to the technical field of the synthesis of pharmaceutical intermediates, and more specifically to a new process synthesis method of 2-mercapto-5-methoxybenzimidazole. Background technique [0002] 2-Mercapto-5-methoxybenzimidazole is a key intermediate for the synthesis of omeprazole, and its structural formula is shown in the following formula: [0003] [0004] In the existing published preparation methods of 2-mercapto-5-methoxybenzimidazole, all nitrate the benzene ring to add the nitro group through a nitration reaction, and reduce to obtain 4-methoxy-1,2-diaminobenzene , And then close the ring to obtain 2-mercapto-5-methoxybenzimidazole. The existing publicly disclosed preparation methods use nitrification, which has a high risk factor and poor operation safety, which improves the safety level and production cost of production, which is not conducive to the promotion and application of industrialization; it is harmful to the oper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/28
Inventor 徐燕军张志攀勾中彪卢芳
Owner 成都泰蓉生物科技有限公司
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