AT38351B - Process for the preparation of the anhydrides of acylsalicylic acids. - Google Patents
Process for the preparation of the anhydrides of acylsalicylic acids.Info
- Publication number
- AT38351B AT38351B AT38351DA AT38351B AT 38351 B AT38351 B AT 38351B AT 38351D A AT38351D A AT 38351DA AT 38351 B AT38351 B AT 38351B
- Authority
- AT
- Austria
- Prior art keywords
- acylsalicylic
- anhydrides
- acids
- preparation
- parts
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 5
- 150000008064 anhydrides Chemical class 0.000 title claims description 5
- 150000007513 acids Chemical class 0.000 title claims 2
- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- -1 sulfur halides Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QSOVSKMNRYAVJR-UHFFFAOYSA-N 2-benzoyloxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1 QSOVSKMNRYAVJR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- OAWXYINGQXLWOE-UHFFFAOYSA-N (2-acetyloxybenzoyl) 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1OC(C)=O OAWXYINGQXLWOE-UHFFFAOYSA-N 0.000 description 1
- XCMXXCOPWNCEHP-UHFFFAOYSA-N 2-(2-carboxyethoxy)benzoic acid Chemical compound OC(=O)CCOC1=CC=CC=C1C(O)=O XCMXXCOPWNCEHP-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
- HLDYXXYLUGPYEY-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OC1=C(C(=O)OC(C2=C(C=CC=C2)OC(C2=CC=CC=C2)=O)=O)C=CC=C1 Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C(=O)OC(C2=C(C=CC=C2)OC(C2=CC=CC=C2)=O)=O)C=CC=C1 HLDYXXYLUGPYEY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
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krystallisiert das neue Anhydrid der Karboxäthylsalizylsäure in glänzenden, zu Drusen und Sternen vereinigten Nadeln, die bei 640 schmelzen.
Beispiel 5 : 242 Teile Benzoylsalizylsäure, 79 Teile Pyridin und 300 Teile Benzol werden mit einer Mischung von 78, 5 Teilen Azetylchlorid und 100 Teilen Benzol versetzt. Unter Er- wärmung scheidet sich salzsaures Pyridin ab. Es wird darauf wie oben beschrieben aufgearbeitet.
Meist scheidet sich nach der Entfernung des Pyridins durch Säure das neue Anhydrid der Benzoylsalizylsäure unmittelbar krystallinisch aus. Anderenfalls empfiehlt es sich, die Benzollösung '/ Tag mit Wasser kräftig durchzurühren, um das als Nebenprodukt gebildete Essigsäureanhydrid zu verseifen, worauf alsdann die Abscheidung des Benzoylsalizylsäureanhydrids stattfindet. Man saugt ab, krystallisiert aus Alkohol um und gewinnt so das Anhydrid als weisses krystallinisches Pulver vom Schmelzpunkt 106 bis 1070.
Beispiel 6 ; Ersetzt man im Beispiel 1 das Pyridin durch 752 Teile Antipyrin, lässt die Mischung 24 Stunden stehen und arbeitet sonst analog auf, so erhält man gleichfalls Azetylsalizylsäureanhydrid.
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The new anhydride of carboxyethylsalicylic acid crystallizes in shiny needles that are united to form drusen and stars, which melt at 640.
Example 5: 242 parts of benzoylsalicylic acid, 79 parts of pyridine and 300 parts of benzene are mixed with a mixture of 78.5 parts of acetyl chloride and 100 parts of benzene. Hydrochloric acid pyridine separates out when heated. It is then worked up as described above.
Usually, after the pyridine has been removed by acid, the new anhydride of benzoylsalicylic acid is immediately precipitated in crystalline form. Otherwise it is advisable to stir the benzene solution vigorously with water per day in order to saponify the acetic anhydride formed as a by-product, whereupon the benzoylsalicylic anhydride is separated out. It is filtered off with suction, recrystallized from alcohol and the anhydride is thus obtained as a white crystalline powder with a melting point of 106 to 1070.
Example 6; If the pyridine in Example 1 is replaced by 752 parts of antipyrine, the mixture is left to stand for 24 hours and otherwise worked up analogously, acetylsalicylic anhydride is likewise obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1907201326D DE201326C (en) | 1907-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT38351B true AT38351B (en) | 1909-08-25 |
Family
ID=5765644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT38351D AT38351B (en) | 1907-08-21 | 1908-09-19 | Process for the preparation of the anhydrides of acylsalicylic acids. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT38351B (en) |
-
1908
- 1908-09-19 AT AT38351D patent/AT38351B/en active
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