US602109A - Israel rods - Google Patents
Israel rods Download PDFInfo
- Publication number
- US602109A US602109A US602109DA US602109A US 602109 A US602109 A US 602109A US 602109D A US602109D A US 602109DA US 602109 A US602109 A US 602109A
- Authority
- US
- United States
- Prior art keywords
- israel
- alkyl
- june
- ether
- citric acid
- 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.)
- Expired - Lifetime
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000005215 alkyl ethers Chemical class 0.000 description 6
- 150000001860 citric acid derivatives Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Definitions
- This invention relates to the manufacture of salts formed bythe action of citric acid upon the alkyl ether of paramidophenol, and particularly with paraphenetidin an'd paranisidin.
- the new salts are obtained by bringing together one molecule of citric acid and one molecule of amidophenol ether in an appropriate solvent like alcohol.
- Citric acid Amidophenol ether. Citrate of amidophenolether.
- the salts thus formed which may be called primary citrates of amidophenol ether, having the general formula G I-I O .NH C H O alkyl,
- One of these amid-like compounds formed by heating citric acid with phenetidin is apolysin, the composition of which corresponds to the 5 formula
- citric acid one molecule
- amidophenol ethyl ether one molecule
- water splits off and apolysin is obtained; but by mixing the said components in a solvent a salt is obtained, which is the object of this application, and this salt is already on the marric acid.
- They are very soluble in water and less so in alcohol. They have a meltingpoint of 186 centigrade.
- the citrate of paranisidin (C I-I O,.NH O H OOH may be obtained in a similar manner. The meltingpoint of 'this latter salt is 186 centigrade.
- citrates of alkyl ethers of paramidophenols are decomposed at a low temperature by the action of alkalies, the components citric alkali and alkyl ethers of paramidophenol being reproduced. All these citrates are very soluble in water, less so in alcohol, and
- citrates of amidophenol alkyl ester are employed in cases of rheumatic and feverish illnesses at doses from 0.6 to two grains per diem. 8
- the primary salts of citric acid with alkyl ethers of paramiclophenol composed according to the formula c n ommc fi o alkyl, being white orystallizing compounds, melting 5 at 186 to 187 centigrade, easily soluble in Water, less soluble in alcohol and almost insoluble in petroleum ether and benzene.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials For Medical Uses (AREA)
Description
are not salts, but amid-like bodies.
NITE- STATES PROCESS OF MAKING SALTS OF PARAM IDOPHENOL.
SPECIFICATION forming part of Letters Patent No. 602,109, dated April 12, 1898.
Application filed June 19,1895. Serial No. 553,297- (Specimens) Patented in England June 8, 1895, No. 11,288; in Belgium June 10, 1895,11'0. 116,014; in Austria, June 10,1895,No-45/3,366,' in France June 11, 1895, No. 248,069, and in Hungary June 14,1895,N0.4,805.
To all whom it mag concern.-
Be it known that I, ISRAEL Roos, chemist, a subject of the German Emperor, residing at Frankfort-on-the-Main, in the Kingdom of Prussia and German Empire, have invented certain new and useful Improvements in the Manufacture of Citrates, Tartrates, and Amygdalates of Paranisidin and Paraphenetidin; and I do hereby declare the following to be a full, clear, and exact description of the invention, such as will enable others skilled in the art to which it appertains to make and use the same.
This invention relates to the manufacture of salts formed bythe action of citric acid upon the alkyl ether of paramidophenol, and particularly with paraphenetidin an'd paranisidin.
For this process a patent has been granted in England, No. 11,288, dated June 8, 1895; in Belgium, No. 116,014, dated June 10, 1895; in France, No. 248,069, dated June 11,1895; in Hungary, No. 4,805, dated June 14, 1895, and in Austria, No. 45 3,366, dated June 10, 1895.
The new salts are obtained by bringing together one molecule of citric acid and one molecule of amidophenol ether in an appropriate solvent like alcohol.
The reaction which takes place is explained by the following equation:
0 11 0, NH,o,H,o alkyl o,H,o,.NH,o,H oa1k 1. Citric acid. Amidophenol ether. Citrate of amidophenolether.
An excess of the base does not alter the reaction, as it-will remain in the solvent. The salts thus formed, which may be called primary citrates of amidophenol ether, having the general formula G I-I O .NH C H O alkyl,
are new and not identical with other alreadyknown compounds which are obtained by heating citric acid with amidophenol ethers. These latter compounds, the constitution of which is expressed by the'equation O H O NH CH 0 alkyl QE 0 .N'HC H Oalkyl-l-H O Citiic acid. Amiclophe nolether. (litry la midopllenol ether. 2
One of these amid-like compounds formed by heating citric acid with phenetidin is apolysin, the composition of which corresponds to the 5 formula By heating citric acid (one molecule) and amidophenol ethyl ether (one molecule) water splits off and apolysin is obtained; but by mixing the said components in a solvent a salt is obtained, which is the object of this application, and this salt is already on the marric acid. They are very soluble in water and less so in alcohol. They have a meltingpoint of 186 centigrade. The citrate of paranisidin (C I-I O,.NH O H OOH may be obtained in a similar manner. The meltingpoint of 'this latter salt is 186 centigrade.
All citrates of alkyl ethers of paramidophenols are decomposed at a low temperature by the action of alkalies, the components citric alkali and alkyl ethers of paramidophenol being reproduced. All these citrates are very soluble in water, less so in alcohol, and
are very nearly insoluble in petroleum ether and in benzene.
The citrates of amidophenol alkyl ester are employed in cases of rheumatic and feverish illnesses at doses from 0.6 to two grains per diem. 8
Having now described my invention, what I claim is- 1. Process for the. manufacture of primary citrates of alkyl ethers of paramidophenols, which consists in dissolving molecular quantio ties of citric acid and amidophenol alkyl ether in a suitable solvent, such as alcohol and.- crystallizing out the salt thus obtained, substantially as described.
2. As new products of manufacture, the primary salts of citric acid with alkyl ethers of paramiclophenol composed according to the formula c n ommc fi o alkyl, being white orystallizing compounds, melting 5 at 186 to 187 centigrade, easily soluble in Water, less soluble in alcohol and almost insoluble in petroleum ether and benzene.
In testimony whereof I have affixed my signature in presence of two witnesses.
ISRAEL ROOS.
l/Vitnessesz JEAN GRUND, FRANK H. MASON.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US602109A true US602109A (en) | 1898-04-12 |
Family
ID=2670744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US602109D Expired - Lifetime US602109A (en) | Israel rods |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US602109A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10102928A1 (en) * | 2001-01-23 | 2002-08-14 | Infineon Technologies Ag | Viterbi decoder |
-
0
- US US602109D patent/US602109A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10102928A1 (en) * | 2001-01-23 | 2002-08-14 | Infineon Technologies Ag | Viterbi decoder |
| DE10102928B4 (en) * | 2001-01-23 | 2004-03-04 | Infineon Technologies Ag | Viterbi decoder and method for decoding |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US602109A (en) | Israel rods | |
| Riebsomer | A study of the reaction products of 1, 2-diamines with aldehydes | |
| US644077A (en) | Acetyl salicylic acid. | |
| US597454A (en) | Walter beacall bishop and alfred bishop | |
| US516707A (en) | Ludwig knorr | |
| US400086A (en) | Oskar iiinsberg | |
| US596797A (en) | Ernst ta uber | |
| US558863A (en) | Tinek | |
| US658446A (en) | Process of obtaining vanillin derivatives. | |
| US574395A (en) | And william ii | |
| US706355A (en) | Acet salicyl phenetidin and process of making same. | |
| US717066A (en) | Piperidin salt and process of making same. | |
| US569425A (en) | Arnaldo piutti | |
| US574396A (en) | And william h | |
| US674687A (en) | Neutral camphorate of phenyldimethylpyrazolon and process of making same. | |
| US576379A (en) | The-main | |
| US569429A (en) | Roberto schiff | |
| US1073855A (en) | Pharmaceutical compound. | |
| JPS6035356B2 (en) | Method for producing pyroglutamyl peptide | |
| US675540A (en) | Methylethylcarbinolurethane and process of making same. | |
| US516766A (en) | Peiedeich krafft and alfred roos | |
| US535846A (en) | Joseph fbeiherr von mering | |
| US659202A (en) | Methylpropylcarbinolurethane and method of making same. | |
| US561730A (en) | Bruno richard seifert | |
| US2498371A (en) | Method for preparing alkylidenesuccinic esters |