US571352A - Emil fischer - Google Patents
Emil fischer Download PDFInfo
- Publication number
- US571352A US571352A US571352DA US571352A US 571352 A US571352 A US 571352A US 571352D A US571352D A US 571352DA US 571352 A US571352 A US 571352A
- Authority
- US
- United States
- Prior art keywords
- uric acid
- set forth
- salt
- ether
- alkyl
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 229940116269 Uric Acid Drugs 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- LEHOTFFKMJEONL-UHFFFAOYSA-N Trioxopurine Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- ZGCYLVDTYUCUNV-UHFFFAOYSA-N CC12NC(NC1(NC(NC2=O)=O)C)=O Chemical compound CC12NC(NC1(NC(NC2=O)=O)C)=O ZGCYLVDTYUCUNV-UHFFFAOYSA-N 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- QGDOQULISIQFHQ-UHFFFAOYSA-N Theacrine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N(C)C(=O)N2C QGDOQULISIQFHQ-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- QFDRTQONISXGJA-UHFFFAOYSA-N 1-methyluric acid Chemical compound O=C1N(C)C(=O)NC2=C1NC(=O)N2 QFDRTQONISXGJA-UHFFFAOYSA-N 0.000 description 2
- 229940108928 Copper Drugs 0.000 description 2
- 240000000280 Theobroma cacao Species 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N Xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000005764 cacao Nutrition 0.000 description 2
- 235000005767 cacao Nutrition 0.000 description 2
- 235000001046 cacaotero Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 235000014987 copper Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- -1 tetramethyl compound Chemical class 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
. NITED STATES ,AT N FICE EMIL FISCHER, OF BERLIN, GERMANY, ASSIGNOR TO 0. F. BOEHRINGIER & SOEHNE, OF WVALDHOF, GERMANY.
METHOD OF OBTAINING TETRA-ALKYL URIC ACID.
SPECIFICATION forming part of Letters Patent N 0. 571,352, dated November 17, 1896.
Application filed June 16, 1896. Serial No. 595,791. (No specimens.) I
To LLZZ whom it may concern:
Be it known that I, EMIL FISCHER, a citi zen of Germany, residing at Berlin, Germany, have invented certain new and useful 1111- provements in the Art of Obtaining Tetra- Alkyl Uric Acids; and I do hereby declare the following to be afull, 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 preparation of the alkyl derivatives of uric acid, and in particular the tetra-alkyl derivatives, having the general formula where All: is used to designate any alkyl or alcohol radical, such as methyl.
The object of the present invention is to enable the tetra-alkyl derivatives to be obtained directly by alkylizing methods from uric acid.
\Vith this object in View my invention, broadly considered, is distinguished by the treatment of the salt of a dialkyl uric acid 0 with a haloid either in an indifferent or inert diluting agent, such as ethyl ether. The said invention, moreover, embraces such further features, steps, and methods as will be set forth hereinafter and pointed out in the 5 claims annexed.
The following will serve as an illustration of the preferred method of carrying out my invention.
To obtain tetramethyl uric acid from a di- 0 methyl uric acid in the dry way, I proceed as follows: I prepare the cuprous salt, which corresponds to the known salt of uric acid, (see Balke, Jom'nalfilr Pmktische Chemie, vol. 47, p. 546,) and whose formula is prob- V ably O I-I N,O (Gl-I .C11 0, (the proportion of Cu found by analysis being 33.7 per cent. in the form of an almost colorless powder by heating an alkaline solution of a dimethyl uric acid with Fchlings solution, that is, an
alkaline solution of potassio-tartrate of cop per in excess. The powder is then dried in cacao at 100 centigrade. One part by weight of the dried powder is mixed with powdered glass and heated to from 120 to 130 centigrade for eight hours with one part by weight 5 5 of methyl iodid and two parts by weight of ether, as a diluent, in a closed vessel. The resulting product is then boiled with water to separate the tetramethyl uric acid. The solution is then evaporated to dryness and the residue is extracted .with chloroform. The tetramethyl uric acid which remains after evaporation of the chloroform is then purified by crystallizing the same from an aqueous or alcoholic solution.
The reaction resulting in the formation of the tetramethyl compound may be expressed in the following equation:
ozngn oucnn ou o +zcn rzc mo on ncu n n o.
The tetra-alkyl compounds may be used in the art of preparing alkyl derivatives of Xanthin, such as trimethyl xanthin or caffein, as set forth in my application for Letters Patent of the United States, Serial No. 595,792, filed June 16, 1896.
Having thus set forth my invention. and what I consider the preferred manner of carrying the same into effect, what I claim, and desire to secure by Letters Patent of the United States, is
1. The process which consists in acting upon the salt of an alkyl derivative of uric acid with ahaloid ether, for the purpose, substantially as set forth.
2. The process which consists in acting upon the salt of a dialkyl uric acid with a haloid ether, for the purpose substantially as set forth.
3. The process which consists in acting upon the cuprous salt of dialkyl uric acid with a haloid ether, for the purpose substantially as set forth.
4:. The process which consists in acting upon the cuprous salt of dimethyl uric acid 5 with methyl iodid to form tetramethyl uric acid. I
5. The process which consists in mixing the copper salt of dimethyl uric acid with powdered glass and heating the same with methyl iodid and ether in the manner and in the proportions, substantially as set forth.
8. The process which consists in Warming an alkaline solution of a dimethyl uric acid with Fehlings solution in excess, then mixing the resulting copper salt of dimethyl uric acid with powdered glass and heating the mixture with methyl iodid and ether, in the manner and in the proportions substantially as set forth.
In testimony whereof I affix my signature in presence of two Witnesses.
EMIL FISCHER. lVitnesses:
WoLn HAUPT, G. PINKUs.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US571352A true US571352A (en) | 1896-11-17 |
Family
ID=2640051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US571352D Expired - Lifetime US571352A (en) | Emil fischer |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US571352A (en) |
-
0
- US US571352D patent/US571352A/en not_active Expired - Lifetime
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