DE221384C - - Google Patents
Info
- Publication number
- DE221384C DE221384C DENDAT221384D DE221384DA DE221384C DE 221384 C DE221384 C DE 221384C DE NDAT221384 D DENDAT221384 D DE NDAT221384D DE 221384D A DE221384D A DE 221384DA DE 221384 C DE221384 C DE 221384C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- salicylic
- acids
- benzene
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 10
- 150000003870 salicylic acids Chemical class 0.000 claims description 4
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- AQOVOMDXZLTVIJ-UHFFFAOYSA-N 2-(2-iodoacetyl)oxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)CI AQOVOMDXZLTVIJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BSVMPWANOMFSPR-UHFFFAOYSA-N 2-iodoacetyl chloride Chemical compound ClC(=O)CI BSVMPWANOMFSPR-UHFFFAOYSA-N 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L Eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 1
- 206010072736 Rheumatic disease Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-N sodium;2-hydroxybenzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1O ABBQHOQBGMUPJH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- -1 α-iodoisovalerylsalicylic acid Chemical compound 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Durch Patent 212422 ist ein Verfahren zur Darstellung von brom acid ylierten Salicylsäuren geschützt. Es wurde nun weiter gefunden, daß man in ähnlicher Weise zu jodacidylierten Salicylsäuren gelangt, wenn man Salicylsäure oder deren Salze mit Halogeniden oder Anhydriden jodierter Säuren der Fettreihe behandelt. Patent 212422 describes a process for the preparation of bromo acid ylated salicylic acids protected. It has now been found that iodoacidylated in a similar manner Salicylic acids are obtained when one salicylic acid or its salts with halides or anhydrides iodized acids of the fat series treated.
Die jodacidylierten Salicylsäuren haben, wie durch Vergleichsversuche festgestellt wurde, in bestimmten Krankheitsfällen eine bessere Wirkung als die entsprechenden jodfreien Präparate; diese bessere Wirkung tritt besonders in solchen Fällen rheumatischer ErkrankungenThe iodoacidylated salicylic acids have, as was determined by comparative tests, in certain cases of illness a better effect than the corresponding iodine-free preparations; this better effect occurs especially in such cases of rheumatic diseases
!•5 zutage, welche an sich auf Jodkalium besser reagieren als auf Salicylsäure.! • 5 revealed, which in themselves are better on potassium iodine than react to salicylic acid.
Beispiel.
Jodacetylsalicylsäure. ·Example.
Iodoacetylsalicylic acid. ·
COOHCOOH
152 Teile salicylsaures Natron werden in152 parts of soda-salicylic acid are in
f. 1000 Teilen trocknem Benzol suspendiert und f. 1000 parts of dry benzene suspended and
bei 14 bis i8° C. unter kräftigem Rühren im Laufe einer halben Stunde mit einem Gemisch von 800 Teilen Benzol und 230 Teilen Jodacetylchlorid (vgl. Berichte 41 [1908], S. 2853, Siedepunkt 51 bis 560 C. bei 16 bis 18 mm Druck) versetzt. Hierauf wird noch etwa 10 Stunden weitergerührt. Die abgeschiedene noch unreine Jodacetylsalicylsäure wird mit Benzol und zur Entfernung von gebildetem Chlornatrium und unverändertem salicylsaurem Natrium mit Wasser gewaschen. Aus etwa 700 warmem Benzol umgelöst, bildet sie weiße Nadeln, die bei ungefähr 1380 unter Zersetzung schmelzen. Jodacetylsalicylsäure ist schwerlöslich in Benzol und nahezu unlöslich in Ligroin. at 14 to i8 ° C. with vigorous stirring over a half hour with a mixture of 800 parts of benzene and 230 parts of iodoacetyl chloride (see. Reports 41 [1908], p 2853, boiling point 51 to 56 0 C. for 16 to 18 mm pressure) offset. Stirring is then continued for about 10 hours. The separated yet impure iodoacetylsalicylic acid is washed with benzene and, to remove the sodium chlorine and unchanged sodium salicylic acid, with water. Recrystallized from about 70 0 warm benzene, it forms white needles which melt at about 138 0 with decomposition. Iodoacetylsalicylic acid is sparingly soluble in benzene and almost insoluble in ligroin.
Die in analoger Weise hergestellte a-Jodisovalerylsalicylsäure The α-iodoisovalerylsalicylic acid prepared in an analogous manner
c H /COOH c H / COOH
66th
^0.CO. CH (J). CH (CHJ2 ^ 0.CO. CH (J). CH (CHJ 2
bildet weiße Kristalle, die unscharf bei 1020 schmelzen.forms white crystals that melt out of focus at 102 0.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE221384C true DE221384C (en) |
Family
ID=482363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT221384D Active DE221384C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE221384C (en) |
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0
- DE DENDAT221384D patent/DE221384C/de active Active
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