SU118225A1 - Meta-aminobenzoic acid iodination method - Google Patents
Meta-aminobenzoic acid iodination methodInfo
- Publication number
- SU118225A1 SU118225A1 SU604536A SU604536A SU118225A1 SU 118225 A1 SU118225 A1 SU 118225A1 SU 604536 A SU604536 A SU 604536A SU 604536 A SU604536 A SU 604536A SU 118225 A1 SU118225 A1 SU 118225A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- meta
- aminobenzoic acid
- acid
- iodination
- solution
- Prior art date
Links
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 title description 6
- 230000026045 iodination Effects 0.000 title description 5
- 238000006192 iodination reaction Methods 0.000 title description 5
- 238000000034 method Methods 0.000 title description 5
- 239000000243 solution Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QMQFFHSJUJDRPG-UHFFFAOYSA-N 3-amino-2,4,6-triiodobenzoic acid Chemical compound NC1=C(I)C=C(I)C(C(O)=O)=C1I QMQFFHSJUJDRPG-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229920008712 Copo Polymers 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- OALWUEBKKOGWOF-UHFFFAOYSA-M [Cl-].[I+] Chemical compound [Cl-].[I+] OALWUEBKKOGWOF-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
2, 4, 6-трииод-З-аминобензойную кислоту (иодкислоту), вл ющуюс основным полупродуктом в синтезе рентгеноконтрастных препаратов «би .лигност («билиграфин) и «урокон получают путем иодировани метааминобензойной кислоты в виде ее хлоргидрата хлористым иодом. Необходимость проводить иодирование в присутствии большого количества сол ной кислоты делает способ мало удобным из-за большой корро .зионной способности среды.2, 4, 6-triiodide-3-aminobenzoic acid (iodine acid), which is the main intermediate in the synthesis of radiopaque preparations, bi biological route (biligraphin) and urocon, is obtained by iodination of meta-amino benzoic acid in the form of its hydrochloride with chloride iodine. The need to carry out iodination in the presence of a large amount of hydrochloric acid makes the method less convenient because of the high corrosion capacity of the medium.
Предлагаемый способ позвол ет проводить иодирование сол нокислой соли мета-амипобензойной кислоты действием нейтрального раствора хлористого иода, вз того в виде комплекса КС1 . JCL Этот способ позвол ет получить конечный продукт с более высоким выходом и уменьшает коррозионность среды и снижает расход иода.The proposed method allows iodination of the hydrochloric acid salt of meta-aminobenzoic acid by the action of a neutral solution of iodine chloride, taken in the form of a complex KC1. JCL This method allows to obtain a final product with a higher yield and reduces the corrosivity of the medium and reduces the consumption of iodine.
Пример. К раствору 86,8 г (0,5 г-мол ) хлоргидрата мета-аминобензойной кислоты в 4 л воды, noMenieHuo.viy в восьмилитровую колбу, имеющую мещалку и термометр, при температуре 20° добавл ют 800 мл 2н раствора КС1 . JC1 в продолжение 2,5 час. так, чтобы к концу прибавлени раствора температура повысилась до и при этой температуре -его выдерживают 2 час. Выпавший осадок иодкислоты отфильтровывают, промывают до исчезновени кислой реакции на конго, отжимают, суспеп .дируют его в 800-900 мл воды при 50° и добавл ют 20%-ный раствор едкого натра до слабощелочной реакции по фенолфталеину, добавл ют 3 г сульфита натри , обрабатывают активированным углем, фильтруют и оставл ют раствор на 15-20 час. Раствор охлаждают до 10° и выделившиес кристаллы натриевой соли иодкислоты отфильтровывают, тщательно отжимают и промывают насыщенным раствором поваренной соли . Затем кристаллы раствор.чют в 4 л воды, обрабатывают при 55° активированным углем с добавкой 1-2 г сульфита натрн , фильтруют и осаждают свободную 2, 4, 6-трииод-З-аминобепзойную кислоту прибавлением 15%-ной со-л ной кислоты до кислой реакции на копго. Иодкислоту фильтруют, про№ 118225- 2 -Example. To a solution of 86.8 g (0.5 gmol) of meta-aminobenzoic acid hydrochloride in 4 liters of water, noMenieHuo.viy, in an eight-liter flask having a blender and a thermometer, at a temperature of 20 °, add 800 ml of 2N KCl solution. JC1 in the continuation of 2.5 hours. so that by the end of the addition of the solution the temperature rises to and at this temperature, it is kept for 2 hours. The precipitated iodine precipitate is filtered off, washed until the acid reaction disappears on Congo, drained, suspended in 800-900 ml of water at 50 ° C, and 20% sodium hydroxide is added to the alkaline reaction by phenolphthalein, 3 g of sodium sulfite are added. , treated with activated carbon, filtered and leave the solution for 15-20 hours. The solution is cooled to 10 ° and the precipitated sodium salt crystals of iodine acid are filtered off, carefully drained and washed with a saturated solution of sodium chloride. Then the solution crystals are counted in 4 l of water, treated at 55 ° with activated carbon with the addition of 1-2 g of sodium sulfite, filtered and the free 2, 4, 6-triyode-3-aminobepsoic acid is precipitated by adding 15% strength. acid before acidic reaction to copo. Iodic acid is filtered, No. 118225-2 -
мывают водой, отжимают и сушат при 60°. Выход196 г (76% от теоретического ). Темп. пл. 194° (с разложением). Продукт пригоден дл синтеза рентгеноконтрастных препаратов.wash with water, wring out and dry at 60 °. Yield 196 g (76% of theoretical). Pace. square 194 ° (with decomposition). The product is suitable for the synthesis of radiopaque drugs.
Предмет изобретени Subject invention
Способ иодировани мета-аминобензойной кислоты в 2, 4, 6-трииод3-аминобензойную кислоту, отличающийс тем, что, с целью уменьшени коррозионности среды, сол нокислую соль мета-аминобензойной кис- оты иодируют комплексом КС . JC1 в нейтральном растворе.The method of iodination of meta-aminobenzoic acid into 2, 4, 6-triiodo-3-aminobenzoic acid, characterized in that, in order to reduce the corrosivity of the medium, the meta-aminobenzoic acid hydrochloride salt is iodized with a KS complex. JC1 in a neutral solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU604536A SU118225A1 (en) | 1958-07-23 | 1958-07-23 | Meta-aminobenzoic acid iodination method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU604536A SU118225A1 (en) | 1958-07-23 | 1958-07-23 | Meta-aminobenzoic acid iodination method |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782575459A Addition SU701586A2 (en) | 1978-02-06 | 1978-02-06 | Grapevine girdling device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU118225A1 true SU118225A1 (en) | 1958-11-30 |
Family
ID=48390297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU604536A SU118225A1 (en) | 1958-07-23 | 1958-07-23 | Meta-aminobenzoic acid iodination method |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU118225A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013865A (en) * | 1988-04-06 | 1991-05-07 | Mallinckrodt, Inc. | Process for the preparation of 2,4,6-triiodo-5-amino-N-alkylisophthalamic acid and 2,4,6-triiodo-5-amino-isophthalamide compounds |
-
1958
- 1958-07-23 SU SU604536A patent/SU118225A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013865A (en) * | 1988-04-06 | 1991-05-07 | Mallinckrodt, Inc. | Process for the preparation of 2,4,6-triiodo-5-amino-N-alkylisophthalamic acid and 2,4,6-triiodo-5-amino-isophthalamide compounds |
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