IES86947B2 - Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method - Google Patents
Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis methodInfo
- Publication number
- IES86947B2 IES86947B2 IES20180091A IES20180091A IES86947B2 IE S86947 B2 IES86947 B2 IE S86947B2 IE S20180091 A IES20180091 A IE S20180091A IE S20180091 A IES20180091 A IE S20180091A IE S86947 B2 IES86947 B2 IE S86947B2
- Authority
- IE
- Ireland
- Prior art keywords
- solution
- benzoic acid
- mass fraction
- washed
- added
- Prior art date
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000005711 Benzoic acid Substances 0.000 title claims abstract description 16
- 235000010233 benzoic acid Nutrition 0.000 title claims abstract description 16
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 16
- 230000017531 blood circulation Effects 0.000 title claims abstract description 10
- 238000003745 diagnosis Methods 0.000 title claims abstract description 10
- 229940079593 drug Drugs 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims abstract description 9
- 238000001308 synthesis method Methods 0.000 title claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 12
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims abstract description 8
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940117389 dichlorobenzene Drugs 0.000 claims abstract description 8
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method, comprises the following steps:3 mol 2-benzene sulfonamide-6-bromo-isophenone and 4-5 mol ethylene glycol monoisopropyl ether were added to the reaction vessel, controlled the stirring speed of 130-160 rpm for 30-40 min, and then raise the temperature of the solution to 40-50 °C, 5-6 mol tetrabutyl titanate was added to the reaction vessel by 5-8 times, which was added every 20-30 min, the temperature was controlled at the 55-60 °C, it was maintained for 130-150 min, then the temperature is reduced to 10-13 °C, the solid is precipitated, filtered and washed with the potassium bromide solution, the pH of the solution is adjusted to 4-5, then the solid is precipitated again, filtered, and washed with the dipropylamine solution, and washed with the dichlorobenzene solution, recrystallizated in ether solution, got the finished o-sulfonamide benzoic acid.
Description
Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method
FIELD OF THE INVENTION
The present invention relates to blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method.
GENERAL BACKGROUND
O-sulfonamide benzoic acid is for the production of sodium sulphate sodium intermediates, saccharin sodium is mainly used as food, beverage sweeteners, and for the diabetic sweet diet as well, it can also be used as a diagnosis of blood circulation and pharmaceutical raw materials, in addition, it can also used as toothpaste, cigarettes, cosmetic flavoring agent and bright chrome plating additives. However, most of the existing synthetic methods are using methylbenzenesulfonic acid and potassium permanganate as reactants, it is complicated and the final yield is not very high. Therefore, it is necessary to propose a new synthetic method for further improving the quality and yield of the product and reducing the byproduct content, it has important economic significance.
SUMMARY
The purpose of the present invention is to provide blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method, comprises the following steps:
(i) 3 mol 2-benzenesulfonamide-6-bromo-isophenone and 4-5 mol ethylene glycol monoisopropyl ether were added to the reaction vessel, controlled the stirring speed of 130-160 rpm for 30-40 min, and then raise the temperature of the solution to 40-50 °C, 5-6 mol tetrabutyl titanate was added to the reaction vessel by 5-8 times, which was added every 20-30 min, the temperature was controlled at the 55-60 °C, it was maintained for 130-150 min, then the temperature is reduced to 10-13 °C, the solid is precipitated, filtered and washed with the potassium bromide solution, the pH of the solution is adjusted to 4-5, then the solid is precipitated again, filtered, and washed with the dipropylamine solution, and washed with the dichlorobenzene solution, recrystallizated in ether solution, got the finished o-sulfonamide benzoic acid; wherein, the ethylene glycol monoisopropyl ether solution in step (i) has a mass fraction of 75 to 83%, and the bromination in step (i) has a mass fraction of 30 to 36%, the mass fraction of the dipropylamine solution in step (i) is 80-85%, the mass fraction of the dich loro benzene solution in step (i) is 86-92%, the mass fraction of the ether solution described in step (i) is 90 to 96%.
Throughout the reaction process can be the following reaction formula:
Advantage of the present invention is that: reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated: blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method.
Embodiment 1 mol 2-benzenesulfonamide-6-bromo-isophenylethanol and 4 mol ethylene glycol monoisopropyl ether with a mass fraction of 75% were added to the reaction vessel, controlled the stirring speed at 130 rpm for 30 min, then raise the temperature of the solution to 40 °C, added 5 mol tetrabutyl titanate to the reaction vessel by 5 times, added it every 20 min, the temperature was control at 55 °C, kept for 130 min, reduced the temperature to 10 “C, the solid was precipitated, filtered, washed with potassium bromide solution with a mass fraction of 30%, adjust the solution pH to 4, precipitated solid again, filtered, washed with dipropylamine solution with a mass fraction of 80%, washed with a mass fraction of 86% dichloro benzene solution, recrystallized in the ether solution with a mass fraction of 90%, got the finished o-sulfonamide benzoic acid 548.73g,theyieldof91%.
Embodiment 2 mol 2-benzenesulfonainide-6-bromo-isophenylethanoI and 4.5 mol ethylene glycol monoisopropyl ether with a mass fraction of 78% were added to the reaction vessel, controlled the stirring speed at 140 rpm for 35 min, then raise the temperature of the solution to 45 °C, added 5.5 mol tetrabutyl titanate to the reaction vessel by 6 times, added it every 25 min, the temperature was control at 57 °C, kept for 140 min, reduced the temperature to 12 C, the solid was precipitated, filtered, washed with potassium bromide solution with a mass fraction of 33%, adjust the solution pH to 4.5, precipitated solid again, filtered, washed with dipropylamine solution with a mass fraction of 82%, washed with a mass fraction of 89% dichlorobenzene solution, recrystallized in the ether solution with a mass fraction of 93%, got the finished o-sulfonamide benzoic acid 560.79g, the yield of 93%.
Embodiment 3 mol 2-benzenesulfonamide-6-bromo-isophenylethanol and 5 mol ethylene glycol monoisopropyl ether with a mass fraction of 83% were added to the reaction vessel, controlled the stirring speed at 160 rpm for 40 min, then raise the temperature of the solution to 50 °C, added 6 mol tetrabutyl titanate to the reaction vessel by 8 times, added it every' 30 min, the temperature was control at 60 °C, kept for 150 min, reduced the temperature to 13 °C, the solid was precipitated, filtered, washed with potassium bromide solution with a mass fraction of 36%, adjust the solution pH to 5, precipitated solid again, filtered, washed with dipropylamine solution with a mass fraction of 85%, washed with a mass fraction of 92% dichlorobenzene solution, recrystallized in the ether solution with a mass fraction of 96%, got the finished o-sulfonamide benzoic acid 578.88g, the yield of 96%.
Claims
Claims (3)
1. Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method, comprises the following steps: (i) 3 mol 2-benzenesulfonamide-6-bromo-isophenone and 4-5 mol ethylene glycol monoisopropyl ether were added to the reaction vessel, controlled the stirring speed of 130-160 rpm for 30-40 min, and then raise the temperature of the solution to 40-50 C, 5-6 mol tetrabutyl titanate was added to the reaction vessel by 5-8 times, which was added every 20-30 min, the temperature was controlled at the 55-60 °C, it was maintained for 130-150 min, then the temperature is reduced to 10-13 °C, the solid is precipitated, filtered and washed with the potassium bromide solution, the pH of the solution is adjusted to 4-5, then the solid is precipitated again, filtered, and washed with the dipropylamine solution, and washed with the dichlorobenzene solution, recrystallizated in ether solution, got the finished o-sulfonamide benzoic acid; wherein, the ethylene glycol monoisopropyl ether solution in step (i) has a mass fraction of 75 to 83%, and the bromination in step (i) has a mass fraction of 30 to 36%, the mass fraction of the dipropylamine solution in step (i) is 80-85%.
2. Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method according to claim 1 wherein the mass fraction of the dichlorobenzene solution in step (i) is 86-92%.
3. Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method according to claim 1 wherein the mass fraction of the ether solution described in step (i) is 90 to 96%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180091A IES86947B2 (en) | 2018-04-03 | 2018-04-03 | Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IES20180091A IES86947B2 (en) | 2018-04-03 | 2018-04-03 | Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IES20180091A2 IES20180091A2 (en) | 2019-01-09 |
| IES86947B2 true IES86947B2 (en) | 2019-01-09 |
Family
ID=65009474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IES20180091A IES86947B2 (en) | 2018-04-03 | 2018-04-03 | Blood circulation diagnosis medication o-sulfonamide benzoic acid synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IES86947B2 (en) |
-
2018
- 2018-04-03 IE IES20180091A patent/IES86947B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IES20180091A2 (en) | 2019-01-09 |
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