IL29324A - New esters of 5-nitroimidazole-2-carboxylic acids and process for their preparation - Google Patents
New esters of 5-nitroimidazole-2-carboxylic acids and process for their preparationInfo
- Publication number
- IL29324A IL29324A IL2932464A IL2932464A IL29324A IL 29324 A IL29324 A IL 29324A IL 2932464 A IL2932464 A IL 2932464A IL 2932464 A IL2932464 A IL 2932464A IL 29324 A IL29324 A IL 29324A
- Authority
- IL
- Israel
- Prior art keywords
- preparation
- nitroimidazole
- esters
- formula
- ethyl
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- LNPSXTPPQBEISL-UHFFFAOYSA-N 5-nitro-1h-imidazole-2-carboxylic acid Chemical class OC(=O)C1=NC=C([N+]([O-])=O)N1 LNPSXTPPQBEISL-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- -1 methyl ethyl Chemical group 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Basic Packing Technique (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
PATENTS AND DESIGNS ORDINANCE SPECIFICATION eaters of 5 carboxylic acids and process for their preparation a Corporation of of do hereby declare the of this invention and in what the same is to be particularly and ascertained in and following This invention relates to new esters of acid which are mediates in certain syntheses of the corresponding logically active The new esters according to invention are presented by the formula wherein and Y are the same or different lower alkyl Examples of such alkyl radicals are isobutyl and the The invention also consists i a process for the preparation of compounds of formula I above represented by the reaction scheme The rst step of the above reaction scheme sists in contacting a compound of II above with a lower in the presence a to form the of formula III A solution of the imidazole in an hydrous lower such as and is contacted with a catalytic amount of a strong and preferably with an alkali or alkaline earth metal Bases as sodium sodium and like are quite of the of formula III takes place at about temperature in from higher up to the reflux temperature of the lower shorter reaction times are The is quite soluble the reaction and is recovered by precipitation therefrom and The of formula III is then converted to a ester of by treatment with aqueous mineral Dilute mineral acids such as and sulfuric acid are normally yields of ester are obtained by allowing an acidified solvent solution of the to stand at room temperature for at least although longer reaction do not have an adverse She resulting esters such as methyl ethyl h and propyl are conveniently recovered in highly by extraction into a organic and sequent removal of the She esters are useful in and which latter substances have substantial activity against turkey The preparation of the nitroimidazole compounds of formula II used as starting materials in the process according to the invention has been disclosed Israel Patent Application The invention is illustrated by the following to it is not Sthyl of is dissolved by warming in 15 of absolute cohol and to the resulting solution there is added 100 of potassium After stirring to dissolve the the solution is allowed to stand 1 hours at room On cooling and scratching profuse precipitation of ethyl resulting is cooled in ice and the solid tered off and twice with cold It is dried to give ethyl Ethyl A solution of g of ethyl in 30 of is treated 30 of I and the mixture allowed to stand for 20 minutes at room reaction mixture is then diluted with about 150 of water and extracted with three 100 portions of ether extracts are dried over and evaporated to dryness in vacuo to substantially pure ethyl latter material is converted to nitroi as follows 500 of ester is dissolved in 5 of warm and the solution added with stirring to 8 of cold concentrated ammonium of and the is allowed to stand in the cold zation is crystals are then removed tion and trashed with cold The product is purified from to Reaction with aqueous of gives meth These are effective against turkey disease fod to at a dose level of about weight in the insufficientOCRQuality
Claims (1)
1. Claim 1 and contacting this latter compound with aqueous mineral A process for preparation of ethyl according to Claim which prises intimately contacting with ethanol in the presence of a strong base to form ethyl and treating this latter with aqueous A process for the preparation of esters of acids according to Claim substantially as deccribed acid esters according to prepared by the according to any of Claims 3 to Dated For the Applicants insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30067563A | 1963-08-07 | 1963-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL29324A true IL29324A (en) | 1968-08-22 |
Family
ID=23160128
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2932464A IL29324A (en) | 1963-08-07 | 1964-07-24 | New esters of 5-nitroimidazole-2-carboxylic acids and process for their preparation |
| IL2175864A IL21758A (en) | 1963-08-07 | 1964-07-24 | Imidazole compounds and methods of preparing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2175864A IL21758A (en) | 1963-08-07 | 1964-07-24 | Imidazole compounds and methods of preparing them |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE651423A (en) |
| BR (1) | BR6461527D0 (en) |
| CH (1) | CH467266A (en) |
| DE (1) | DE1470080A1 (en) |
| DK (4) | DK108153C (en) |
| FR (1) | FR1583154A (en) |
| GB (2) | GB1077692A (en) |
| IL (2) | IL29324A (en) |
| NL (2) | NL139524B (en) |
| NO (1) | NO116163B (en) |
| SE (1) | SE325273B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676439A (en) * | 1971-04-13 | 1972-07-11 | Hoffmann La Roche | 5,6-dihydro-8,8-dimethyl-3-nitro-8h imidazo(2-1-c) (1,4)oxazine |
| DE102022003986A1 (en) | 2021-10-01 | 2023-04-06 | Tobias Schmallenbach | Multifunctional bag |
-
0
- NL NL139524D patent/NL139524A/xx unknown
-
1964
- 1964-07-24 IL IL2932464A patent/IL29324A/en unknown
- 1964-07-24 IL IL2175864A patent/IL21758A/en unknown
- 1964-08-04 GB GB3156964A patent/GB1077692A/en not_active Expired
- 1964-08-04 GB GB3577766A patent/GB1077696A/en not_active Expired
- 1964-08-05 DK DK492465A patent/DK108153C/en active
- 1964-08-05 BE BE651423D patent/BE651423A/xx unknown
- 1964-08-05 DK DK492265A patent/DK109264C/en active
- 1964-08-05 DK DK387064A patent/DK108499C/en active
- 1964-08-05 DK DK492365A patent/DK108229C/en active
- 1964-08-06 DE DE19641470080 patent/DE1470080A1/en active Pending
- 1964-08-06 FR FR1583154D patent/FR1583154A/fr not_active Expired
- 1964-08-06 BR BR16152764A patent/BR6461527D0/en unknown
- 1964-08-06 NO NO15428564A patent/NO116163B/no unknown
- 1964-08-06 SE SE955264A patent/SE325273B/xx unknown
- 1964-08-07 CH CH1035764A patent/CH467266A/en unknown
- 1964-08-07 NL NL6409120A patent/NL139524B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK109264C (en) | 1968-04-08 |
| NL139524A (en) | |
| DK108153C (en) | 1967-09-25 |
| NO116163B (en) | 1969-02-10 |
| IL21758A (en) | 1968-08-22 |
| BE651423A (en) | 1965-02-05 |
| NL139524B (en) | 1973-08-15 |
| DK108499C (en) | 1967-12-27 |
| GB1077696A (en) | 1967-08-02 |
| SE325273B (en) | 1970-06-29 |
| CH467266A (en) | 1969-01-15 |
| NL6409120A (en) | 1965-02-08 |
| BR6461527D0 (en) | 1973-07-17 |
| DE1470080A1 (en) | 1970-01-02 |
| GB1077692A (en) | 1967-08-02 |
| FR1583154A (en) | 1969-10-24 |
| DK108229C (en) | 1967-10-23 |
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| SU427016A1 (en) | METHOD FOR OBTAINING 4H-3,1-BENZOXAZIN-4-OH-2-CARBIC ACID AMIDES1 The invention relates to the preparation of the 4H-3,1-benzoxazin-4-one-2-amides - carboxylic acid. These amides are not described in the literature, their method of preparation is not known. Chemically, they are highly active compounds and are of interest as intermediates for organic sietez, including for the production of biologically active compounds. In particular, on the basis of these amides, amides of 4 (3H) -quinazolo; n-2-carboxylic acid can be obtained, which, according to literature data, represent HiHTOpec as drugs with P-vitamin activity. In the literature A 4N-3, .1-benzoxazn-4-one-2-carboxylic acid ester preparation method is known to react oxamoyl anthranilic acid ethyl ester with acetic anhydride, followed by isolation of the products by a known method. However, the 4H-3,1-benzoxazium-4-one-2-carboxylic acid amides, as the method of their preparation, were not previously known. A method for preparing the 4H-3,1-benzoxazip-4-one-2-carboxylic acid amides is proposed. of the general formula ICONHR10, where R is hydrogen, normal or isoalkyl, consisting in the fact that the amide of oxamoyl anthranilic acid of the general formula . Methylamide 4H-3,1-benzoxazip-4-one-2-carboxylic acid. 8 g of 1M-1 methyl-ox-M'OIyl "tra". Methyl acid (II, R-CH3) in 16 ml of acetic angndrum is heated under reflux. After 10 minutes from the start of heating, the acid is completely dissolved, heating is continued for another 10 minutes. Upon cooling, a precipitate is released. To the reaction mass was added 10 ml of absolute ether. Sediment filter | |
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