DE266121C - - Google Patents
Info
- Publication number
- DE266121C DE266121C DENDAT266121D DE266121DA DE266121C DE 266121 C DE266121 C DE 266121C DE NDAT266121 D DENDAT266121 D DE NDAT266121D DE 266121D A DE266121D A DE 266121DA DE 266121 C DE266121 C DE 266121C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- parts
- urethane
- alcohol
- bromoacetyl
- 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
- -1 glycolyl urethane bromine Chemical compound 0.000 claims description 14
- WMKXMEBGSGFRMT-UHFFFAOYSA-N ethyl N-(2-chloroacetyl)carbamate Chemical compound CCOC(=O)NC(=O)CCl WMKXMEBGSGFRMT-UHFFFAOYSA-N 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- JHJLBTNAGRQEKS-UHFFFAOYSA-M Sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- ZTCLDQRGRNZRFS-UHFFFAOYSA-N ethyl N-(2-bromoacetyl)carbamate Chemical compound CCOC(=O)NC(=O)CBr ZTCLDQRGRNZRFS-UHFFFAOYSA-N 0.000 description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 229940075581 sodium bromide Drugs 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- IIOUXXMRKBVCNM-UHFFFAOYSA-N 2-bromo-N-carbamoylacetamide Chemical compound NC(=O)NC(=O)CBr IIOUXXMRKBVCNM-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- BRUZQRBVNRKLJG-UHFFFAOYSA-N 2-methylpropyl carbamate Chemical compound CC(C)COC(N)=O BRUZQRBVNRKLJG-UHFFFAOYSA-N 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- SYWSERLZKPGKDI-UHFFFAOYSA-N methyl N-(2-chloroacetyl)carbamate Chemical compound COC(=O)NC(=O)CCl SYWSERLZKPGKDI-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004025 sodium salicylate Drugs 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
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Bei weiteren Versuchen ist gefunden worden, daß sich bei der Reaktion des Hauptpatentes an Stelle des Bromacetylharnstoffes mit gutem Erfolg Brom- und Chloracetylurethane verwenden lassen, und zwar verläuft hierbei die Reaktion rascher und glatter als bei dem Verfahren des Hauptpatentes. Außer dem in der Literatur bereits beschriebenen Chloracetylurethan und Bromacetylurethan sind noch einige andere Halogenurethane hergestellt und nachstehend beschrieben.In further experiments it has been found that in the reaction of the main patent Use bromo- and chloroacetyl urethanes in place of the bromoacetylurea with good success let, and that here the reaction proceeds faster and smoother than in the process of the main patent. Except for the chloroacetyl urethane already described in the literature and bromoacetyl urethane, some other halo urethanes are prepared and described below.
So erhält man durch Einwirkung von Chloracetylchlorid auf carbaminsaures Methyl den Chloracetylcarbaminsäurernethylester, der bei 145 ° schmilzt.So obtained by exposure to chloroacetyl chloride on methyl carbamic acid the methyl chloroacetylcarbamic acid, which is used in 145 ° melts.
Läßt man anstatt Chloracetylchlorid Bromacetylchlorid oder Bromacetylbromid auf carbaminsaures Methyl einwirken, so erhält man in glatter Weise den Bromacetylcarbaminsäuremethylester, der in seinen Eigenschaften dem entsprechenden gechlorten Ester nahesteht und bei 148° seinen Schmelzpunkt hat. Der Chloracetylcarbaminsäureisobutylester, welcher durch Einwirkung von Chloracetylchlorid auf Carbaminsäureisobutylester entsteht, schmilzt bei 78°, der ähnlich dargestellte Bromacetylcarbaminsäureisobutylester bei 87 °.If instead of chloroacetyl chloride, bromoacetyl chloride or bromoacetyl bromide is left on carbamic acid Act methyl, one gets in a smooth way the bromoacetylcarbamic acid methyl ester, which is close in its properties to the corresponding chlorinated ester and has its melting point at 148 °. The isobutyl chloroacetylcarbamic acid ester, which is formed by the action of chloroacetyl chloride on isobutyl carbamate, melts at 78 °, the isobutyl bromoacetylcarbamate shown similarly at 87 °.
Diese Halogenacylurethane können auch durch Einwirkung von Halogenfettsäureestern auf die entsprechenden 2V«-Urethane erhalten werden.These haloacyl urethanes can also be produced by the action of halo fatty acid esters to the corresponding 2V «urethanes are obtained.
4040
An Hand des Beispieles des Hauptpatentes läßt sich die Reaktion durch nachstehende Gleichung ausdrücken:Using the example of the main patent, the reaction can be illustrated by the following Express equation:
C2H6O-CO-NH-CO-CH2BrC 2 H 6 O-CO-NH-CO-CH 2 Br
+ NaCOO CH3 + NaCOO CH 3
= C2H6O -CO -NH -CO — CH2- 0OC - CHZ + Na Br.= C 2 H 6 O -CO -NH -CO-CH 2 -OC-CH Z + Na Br.
210 Teile Bromacetylurethan und 136 Teile essigsaures Natron werden mit 1500 Teilen hochprozentigem Alkohol 4 bis 6 Stunden am Rückflußkühler gekocht. Nachdem vom abgeschiedenen Bromnatrium abfiltriert ist, engt man den Alkohol ein und läßt das Reaktionsprodukt auskristallisieren. Das Acetylglykolurethan bildet farblose Nadeln, welche unscharf bei 98 ° schmelzen. Es ist in Wasser wie auch Alkohol leicht löslich.210 parts of bromoacetyl urethane and 136 parts Acetic acid sodium is refluxed with 1500 parts of high percentage alcohol for 4 to 6 hours cooked. After the precipitated sodium bromide has been filtered off, the alcohol is concentrated and the reaction product is allowed to crystallize out. The acetyl glycol urethane forms colorless needles, which melt blurred at 98 °. It is easily soluble in water like alcohol.
473 Teile bromisovaleriansaures Natrium und 525 Teile Bromacetylurethan werden mit 2500 Teilen hochprozentigem Alkohol nach Beispiel ι gekocht und weiter verarbeitet. Das Bromisovalerianylglykolylurethan bildet farblose Nädelchen, welche bei 103 ° schmelzen. Dasselbe ist in Wasser schwer löslich, wird dagegen leicht von Sprit und Äther aufgenommen. 473 parts of sodium bromoisovaleric acid and 525 parts of bromoacetyl urethane are added 2500 parts of high percentage alcohol cooked according to Example ι and processed further. That Bromisovalerianylglykolylurethan forms colorless needles which melt at 103 °. It is sparingly soluble in water, but it is easily absorbed by fuel and ether.
Bei spiel 3.Example 3.
160 Teile salicylsaures Natrium und 210 Teile160 parts of sodium salicylate and 210 parts
Bromacetylurethan werden mit 1500 Teilen Alkohol in nach Beispiel 1 beschriebener Weise gekocht und verarbeitet. Das Salicylsäureglykolylurethan kristallisiert beim ErkaltenBromoacetyl urethane are made with 1500 parts of alcohol cooked and processed in the manner described in Example 1. The salicylic acid glycolyl urethane crystallizes on cooling
. aus, wird abgenutscht und behufs Entfernung des Bromnatriums mit Wasser gewaschen.. off, is suction filtered and washed with water to remove the sodium bromide.
Der Körper schmilzt bei 1460, ist unlöslich in Wasser und Äther, leicht löslich in warmem Alkohol.The body melts at 146 0 , is insoluble in water and ether, easily soluble in warm alcohol.
203 g bromisovaleriansaures Natron und 800 g Alkohol abs. werden mit 151 g Chloracetylcarbaminsäuremethylester 3 bis 4 Stunden am Rückflußkühler gekocht, das sich ausscheidende Kochsalz wird abfiltriert und die Spritlauge etwas eingeengt. Aus der konzentrierten Lauge kristallisiert der Bromisovalerylglykolylcarbaminsäuremethylester aus und schmilzt bei 90 °, er ist löslich in Sprit und Äther, dagegen unlöslich in Wasser.203 g of sodium bromide valerate and 800 g of alcohol abs. are with 151 g of chloroacetylcarbamic acid methyl ester Boiled for 3 to 4 hours on the reflux condenser, the precipitating common salt is filtered off and the Lye somewhat concentrated. The methyl bromoisovalerylglycolylcarbamic acid crystallizes from the concentrated liquor and melts at 90 °, it is soluble in fuel and ether, but insoluble in water.
160 Teile salicylsaures Natron werden mit 151 Teilen Chloracetylcarbaminsäuremethylester in etwa 1000 Teilen Sprit einige Stunden gekocht, die Lauge eingedampft, vom Kochsalz befreit und zur Kristallisation beiseite gestellt. Der Salicylsäureglykolylcarbaminsäuremethylester ist ziemlich leicht löslich in Wasser und Alkohol und schmilzt bei 150°.160 parts of sodium salicylic acid are mixed with 151 parts of methyl chloroacetylcarbamic acid Boiled in about 1000 parts of fuel for a few hours, the lye evaporated from the table salt freed and set aside for crystallization. The salicylic acid glycolylcarbamic acid methyl ester is quite easily soluble in water and alcohol and melts at 150 °.
Bei obigen Reaktionen kann man an Stelle von Alkohol auch Benzol oder Toluol verwenden. In the above reactions, benzene or toluene can also be used instead of alcohol.
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE266121C true DE266121C (en) |
Family
ID=523290
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT266121D Active DE266121C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE266121C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004113270A2 (en) * | 2003-06-18 | 2004-12-29 | Astrazeneca Ab | Propionic acid derivatives useful in the treatment of lipid disorders |
US7462644B2 (en) | 2002-12-21 | 2008-12-09 | Astrazeneca Ab | Therapeutic agents |
US7514471B2 (en) | 2001-12-19 | 2009-04-07 | Astrazeneca Ab | Substituted phenylpropionic acid derivatives as agonists to human peroxisome proliferator-activated receptor α (PPAR) |
-
0
- DE DENDAT266121D patent/DE266121C/de active Active
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7488844B2 (en) | 2001-12-19 | 2009-02-10 | Astrazeneca Ab | Therapeutic agents |
US7514471B2 (en) | 2001-12-19 | 2009-04-07 | Astrazeneca Ab | Substituted phenylpropionic acid derivatives as agonists to human peroxisome proliferator-activated receptor α (PPAR) |
US7462644B2 (en) | 2002-12-21 | 2008-12-09 | Astrazeneca Ab | Therapeutic agents |
WO2004113270A2 (en) * | 2003-06-18 | 2004-12-29 | Astrazeneca Ab | Propionic acid derivatives useful in the treatment of lipid disorders |
WO2004113270A3 (en) * | 2003-06-18 | 2005-03-31 | Astrazeneca Ab | Propionic acid derivatives useful in the treatment of lipid disorders |
AU2004249409B2 (en) * | 2003-06-18 | 2008-05-29 | Astrazeneca Ab | Propionic acid derivatives useful in the treatment of lipid disorders |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE266121C (en) | ||
DE2004280C3 (en) | Procedure for crystallizing vitamin D deep 3 | |
DE1009623B (en) | Process for the preparation of ª ‡ -oxy-1,2,5,6-tetrahydrobenzylphosphinous acid or its alkali metal salts | |
DE946804C (en) | Process for the production of sulfur-containing extracts of barbituric acid | |
DE875807C (en) | Process for the preparation of dialkylamides of aliphatic or aromatic carboxylic acids | |
DE400970C (en) | Process for the preparation of compounds from benzene dicarboxylic acids and salicylic acid or their substitution products | |
DE291614C (en) | ||
DE1034189B (en) | Process for the preparation of 2-hydroxy-4-aminobenzoic acid phenyl ester | |
AT70874B (en) | Process for the preparation of salts of betaine. | |
DE335993C (en) | Process for the production of hydantoins | |
DE481733C (en) | Process for the preparation of C, C-disubstituted derivatives of barbituric acid | |
DE838001C (en) | Process for the production of condensate connections | |
DE929729C (en) | Process for purifying dehydrocholic acid | |
DE650431C (en) | Process for the preparation of trisubstituted barbituric acids | |
DE622405C (en) | Process for the preparation of unsaturated lactones of the alicyclic series | |
DE621964C (en) | Process for the production of barbituric acids | |
DE266788C (en) | ||
DE365682C (en) | Process for the preparation of the acetyl compounds of the quinine esters of aromatic oxycarboxylic acids | |
DE1468344A1 (en) | UNSATABLED ACIDS AND THE METHOD OF MANUFACTURING THEREOF | |
DE671461C (en) | Process for the preparation of carbamic acid esters of choline halides | |
DE557247C (en) | Process for the preparation of sulfhydryl compounds of carbohydrates | |
AT238161B (en) | Process for the preparation of new acylhydrazones | |
AT164549B (en) | Process for the production of sterol degradation products | |
DE946623C (en) | Process for the separation of racemic threo-1-phenyl-2-amino-1, 3-propanediol into its optically active antipodes | |
AT129783B (en) | Process for the preparation of 2-oxymethylbenzimidazolaric acids. |