AU2016102189A4 - Methenamine drug intermediates N-benzoyl glycine synthesis method - Google Patents
Methenamine drug intermediates N-benzoyl glycine synthesis method Download PDFInfo
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- AU2016102189A4 AU2016102189A4 AU2016102189A AU2016102189A AU2016102189A4 AU 2016102189 A4 AU2016102189 A4 AU 2016102189A4 AU 2016102189 A AU2016102189 A AU 2016102189A AU 2016102189 A AU2016102189 A AU 2016102189A AU 2016102189 A4 AU2016102189 A4 AU 2016102189A4
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Abstract
Methenamine drug intermediates N- benzoyl glycine synthesis method, comprising the following steps: equipped with a stiffer and a dropping funnel, the reaction vessel was added 0.34 mol glycine (3), 300ml sodium sulfite solution, controlling the stirring speed 130-160rpm, slowly added dropwise 0.39-0.40mol benzamide solution (2), the stirring was continued for 80-120min, the temperature of the solution is reduced to 10 - 15 C, added 200--230ml oxalic acid solution, adjusting the pH of the solution to 5-6, allowed to stand for 8-9 h, the precipitated solid was filtered and the solid was added to 200ml dimethyl amine solution, refluxed for 30-50min, reduced the solution temperature to 5 - 8 0C, suction filtered, the filter cake was washed with dimethylamine solution, recrystallization with 700ml potassium bromide solution, molecular sieves bleaching, filtration, the solution temperature is reduced to 1-3 0C, crystals precipitation, suction filtration, dehydration with dehydrating agent, got N- benzoyl glycine.
Description
Methenamine drug intermediates N-benzoyl glycine synthesis method
TECHNICAL FIELD
The present invention relates to methenamine drug intermediates N- benzoyl glycine synthesis method.
BACKGROUND ART
Methenamine can be used as curing agent a catalyst and a blowing agent of amino plastic of resin and plastic, and as rubber vulcanization accelerator (accelerator H), textiles shrink-proof agent, organic synthesis of raw materials in the pharmaceutical industry It is used to produce chloramphenicol and for the manufacture of pesticides. It is also used for making fungicides, medicinal, acidic urine after oral administration in case of decomposition of formaldehyde into sterilization for mild urinary tract infection; it can mix with caustic soda and sodium phenol for gas masks as phosgene absorber. N-benzoyl glycine as methenamine drug intermediates, its synthesis method is of great economic significance for improving drug synthesis product quality, reducing the by-product content.
SUMMARY OF THE INVENTION
Object of the present invention is to provide methenamine drug intermediates N- benzoyl glycine synthesis method, comprising the following steps: (i) equipped with a stirrer and a dropping funnel, the reaction vessel was added 0.34 mol glycine (3), 300ml sodium sulfite solution, controlling the stirring speed 130-160rpm, slowly added dropwise 0.39-0.40mol benzamide solution (2), the stirring was continued for 80-120min, the temperature of the solution is reduced to 10 - 15 °C, added 200—230ml oxalic acid solution, adjusting the pH of the solution to 5-6, allowed to stand for 8-9 h, the precipitated solid was filtered and the solid was added to 200ml dimethyl amine solution, refluxed for 30-50min, reduced the solution temperature to 5 - 8 °C, suction filtered, the filter cake was washed with dimethylamine solution, recrystallization with 700ml potassium bromide solution, molecular sieves bleaching, filtration, the solution temperature is reduced to 1-3 °C, crystals precipitation, suction filtration, dehydration with dehydrating agent, got N- benzoyl glycine (1); wherein sodium sulfite solution in step (i) has a mass fraction of 30-35%, oxalic acid solution in step (i) has a mass fraction of 15-20%, dimethyl amine solution in step (i) has a mass fraction of 90-95%, potassium bromide solution in step (i) has a mass fraction of 40-45%, dehydrating agent in step (i) is any one of anhydrous potassium carbonate or phosphorus pentoxide.
The throughout reaction process can be summarized using the following reaction formula:
(2) P> (1)
Advantage of the present invention is that: the reaction intermediate links are reduced, reducing the reaction temperature and reaction time, improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION
Embodiment 1
Equipped with a stirrer and a dropping funnel, the reaction vessel was added 0.34 mol glycine (3), 300ml sodium sulfite solution with a mass fraction of 30%, controlling the stirring speed 130 rpm, slowly added dropwise 0.39 mol benzamide solution (2), the stirring was continued for 80 min, the temperature of the solution is reduced to 10 °C, added 200 ml oxalic acid solution with a mass fraction of 15%, adjusting the pH of the solution to 5, allowed to stand for 8 h, the precipitated solid was filtered and the solid was added to 200ml dimethyl amine solution with a mass fraction of 90%, refluxed for 30min, reduced the solution temperature to 5 °C, suction filtered, the filter cake was washed with dimethylamine solution, recrystallization with 700ml potassium bromide solution with a mass fraction of 40%, molecular sieves bleaching, filtration, the solution temperature is reduced to 1 °C, crystals precipitation, suction filtration, dehydration with phosphorus pentoxide dehydrating agent, got N- benzoyl glycine 50.51 g, yield 83%.
Embodiment 2
Equipped with a stirrer and a dropping funnel, the reaction vessel was added 0.34 mol glycine (3), 300ml sodium sulfite solution with a mass fraction of 32%, controlling the stirring speed 150 rpm, slowly added dropwise 0.395 mol benzamide solution (2), the stirring was continued for 90 min, the temperature of the solution is reduced to 12 °C, added 220 ml oxalic acid solution with a mass fraction of 17%, adjusting the pH of the solution to 5, allowed to stand for 8 h, the precipitated solid was filtered and the solid was added to 200ml dimethyl amine solution with a mass fraction of 92%, refluxed for 40min, reduced the solution temperature to 6 °C, suction filtered, the filter cake was washed with dimethylamine solution, recrystallization with 700ml potassium bromide solution with a mass fraction of 42%, molecular sieves bleaching, filtration, the solution temperature is reduced to 2 °C, crystals precipitation, suction filtration, dehydration with phosphorus pentoxide dehydrating agent, got N- benzoyl glycine 52.34 g, yield 86%.
Embodiment 3
Equipped with a stirrer and a dropping funnel, the reaction vessel was added 0.34 mol glycine (3), 300ml sodium sulfite solution with a mass fraction of 35%, controlling the stirring speed 160 rpm, slowly added dropwise 0.4 mol benzamide solution (2), the stirring was continued for 120 min, the temperature of the solution is reduced to 15 °C, added 220 ml oxalic acid solution with a mass fraction of 20%, adjusting the pH of the solution to 5, allowed to stand for 8 h, the precipitated solid was filtered and the solid was added to 200ml dimethyl amine solution with a mass fraction of 92%, refluxed for 50min, reduced the solution temperature to 8 °C, suction filtered, the filter cake was washed with dimethylamine solution, recrystallization with 700ml potassium bromide solution with a mass fraction of 42%, molecular sieves bleaching, filtration, the solution temperature is reduced to 3 °C, crystals precipitation, suction filtration, dehydration with potassium carbonate dehydrating agent, got N- benzoyl glycine 55.38 g, yield 91%.
While a number of preferred embodiments have been described, it will be appreciated by persons skilled in the art that numerous variations and/or modifications may be made to the invention without departing from the spirit or scope of the invention as broadly described. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive.
Claims (4)
1. Methenamine drug intermediates N-benzoyl glycine synthesis method, comprising the following steps: (i) equipped with a stirrer and a dropping funnel, the reaction vessel was added 0.34 mol glycine (3), 300ml sodium sulfite solution, controlling the stirring speed 130-160rpm, slowly added dropwise 0.39-0.40mol benzamide solution (2), the stirring was continued for 80-120min, the temperature of the solution is reduced to 10-15 °C, added 200—230ml oxalic acid solution, adjusting the pH of the solution to 5-6, allowed to stand for 8-9 h, the precipitated solid was filtered and the solid was added to 200ml dimethyl amine solution, refluxed for 30-50min, reduced the solution temperature to 5-8°C, suction filtered, the filter cake was washed with dimethylamine solution, recrystallization with 700ml potassium bromide solution, molecular sieves bleaching, filtration, the solution temperature is reduced to 1-3 °C, crystals precipitation, suction filtration, dehydration with dehydrating agent, got N- benzoyl glycine (1); wherein sodium sulfite solution in step (i) has a mass fraction of 30-35%, oxalic acid solution in step (i) has a mass fraction of 15-20%.
2. Methenamine drug intermediates N- benzoyl glycine synthesis method according to claim 1 wherein dimethyl amine solution in step (i) has a mass fraction of 90-95%.
3. Methenamine drug intermediates N- benzoyl glycine synthesis method according to claim 1 wherein potassium bromide solution in step (i) has a mass fraction of 40-45%.
4. Methenamine drug intermediates N- benzoyl glycine synthesis method according to claim 1 wherein dehydrating agent in step (i) is any one of anhydrous potassium carbonate or phosphorus pentoxide.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510975857.XA CN105646264A (en) | 2015-12-23 | 2015-12-23 | Synthetic method of urotropine medicament intermediate N-benzoyl glycine |
| CN201510975857X | 2015-12-23 | ||
| CN2016108139581 | 2016-09-11 | ||
| CN201610813958.1A CN106397245A (en) | 2015-12-23 | 2016-09-11 | Synthesis method of urotropine drug intermediate N-benzoylglycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2016102189A4 true AU2016102189A4 (en) | 2017-02-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016102189A Ceased AU2016102189A4 (en) | 2015-12-23 | 2016-12-22 | Methenamine drug intermediates N-benzoyl glycine synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2016102189A4 (en) |
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2016
- 2016-12-22 AU AU2016102189A patent/AU2016102189A4/en not_active Ceased
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| FGI | Letters patent sealed or granted (innovation patent) | ||
| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |