DE102892C - - Google Patents
Info
- Publication number
- DE102892C DE102892C DENDAT102892D DE102892DA DE102892C DE 102892 C DE102892 C DE 102892C DE NDAT102892 D DENDAT102892 D DE NDAT102892D DE 102892D A DE102892D A DE 102892DA DE 102892 C DE102892 C DE 102892C
- Authority
- DE
- Germany
- Prior art keywords
- lactyl
- amidophenol
- amidophenoxylacetamide
- water
- acet
- 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
- VXIVSQZSERGHQP-UHFFFAOYSA-N Chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LCZDCKMQSBGXAH-AWEZNQCLSA-N 3-[[3-[(2S)-2-amino-2-carboxyethyl]-5-methyl-2,6-dioxopyrimidin-1-yl]methyl]-5-phenylthiophene-2-carboxylic acid Chemical compound O=C1C(C)=CN(C[C@H](N)C(O)=O)C(=O)N1CC1=C(C(O)=O)SC(C=2C=CC=CC=2)=C1 LCZDCKMQSBGXAH-AWEZNQCLSA-N 0.000 description 1
- 241000237988 Patellidae Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N p-acetaminophenol Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 12: Chemische Verfahren und Apparate.CLASS 12: Chemical processes and apparatus.
Zusatz zum Patente JMi 102315 vom g. Februar 1898.Addition to the patent JMi 102315 from g. February 1898.
Längste Dauer: 8. Februar 1913.Longest duration: February 8, 1913.
In der Patentschrift Nr. 102315 wird ein Verfahren beschrieben, durch Einwirkung von Chloracetamid auf Salze des Acet-p-amidophenols zum Acet - ρ - amidophenoxylacetamid zu gelangen. Es wurde nun gefunden, dafs auch andere Acidylderivate des p-Amidophenols in gleicher Weise mit Chloracetamid reagiren. Ein durch seine Leichtlöslichkeit in Wasser sich auszeichnendes Product erhält man durch Verwendung von Lactyl-p-amidophenol an Stelle des Acet-p-amidophenols in dem durch das Patent Nr. 102315 geschützten Verfahren. Man verfährt zur Darstellung von Lactyl-p-Amidophenoxylacetamid z. B. wie folgt:In patent specification No. 102315 a Process described by the action of chloroacetamide on salts of acet-p-amidophenol to get to the acet - ρ - amidophenoxylacetamide. It has now been found that other acidyl derivatives of p-amidophenol also react in the same way with chloroacetamide. A product which is distinguished by its easy solubility in water is obtained through Use of lactyl-p-amidophenol instead of acet-p-amidophenol in the by the patent no. 102315 protected process. The procedure for the preparation of lactyl-p-amidophenoxylacetamide z. B. as follows:
18,1 kg Lactyl-p-amidophenol werden in 55 kg Alkohol und 19 kg Kalilauge (von 29,5 pCt. K O H) gelöst und mit 9,35 kg Chloracetamid 6 bis 8 Stunden am Rückflufskühler im Wasserbade zum Sieden erhitzt. Sodann destillirt man- den Alkohol zum gröfsten Theile ab und scheidet aus dem Rückstand durch Wasserzusatz das Lactyl-p-amidophenoxylacetamid _ ab. Das Rohproduct wird durch Behandeln mit Alkali von unzersetztem Acetamidophenol befreit und durch Umkrystallisiren aus Wasser unter Zusatz von Thierkohle gereinigt. Man erhält die neue Verbindung so in Form farbloser Nadeln vom Schmelzpunkt 175 bis 177° C. Die Stickstoffbestimmung ergab folgende Zahlen:18.1 kg of lactyl-p-amidophenol are dissolved in 55 kg of alcohol and 19 kg of potassium hydroxide solution (of 29.5 pCt. KOH) and heated to boiling with 9.35 kg of chloroacetamide for 6 to 8 hours on a reflux condenser in a water bath. Most of the alcohol is then distilled off, and the lactyl-p-amidophenoxylacetamide is separated from the residue by adding water. The crude product is freed from undecomposed acetamidophenol by treatment with alkali and purified by recrystallization from water with the addition of animal charcoal. The new compound is obtained in the form of colorless needles with a melting point of 175 to 177 ° C. The nitrogen determination gave the following figures:
0,3137 g Substanz lieferten 32,5 ecm Stickstoff bei 190 C. und 766 mm Barometerstand, entsprechend i2,oipCt. N; berechnet für CnH14N2 O4 limpet. N. 0.3137 g of substance delivered 32.5 cc nitrogen at 19 0 C. and 766 mm barometric pressure, corresponding to i2, oipCt. N; calculated for C n H 14 N 2 O 4 limpet. N.
Das Lactyl-p-amidophenoxylacetamidThe lactyl-p-amidophenoxylacetamide
r rr /NH-CO-CH- OH-CH3 (4)
υ6Λ4\ ο. C H2 C O- N H2 (ι) r rr / NH-CO-CH- OH-CH 3 (4)
υ 6 Λ 4 \ ο. CH 2 C O- NH 2 (ι)
ist bei 25° C. in 83,5 Theilen Wasser löslich, bei Körperwärme noch erheblich leichter. In Alkohol ist es leicht löslich. Es dient zur Verwendung in der Medicin.is soluble in 83.5 parts of water at 25 ° C. considerably lighter at body heat. It is easily soluble in alcohol. It is used for Use in Medicin.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102892C true DE102892C (en) |
Family
ID=373438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT102892D Active DE102892C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE102892C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426885A (en) * | 1942-10-09 | 1947-09-02 | Lowell B Kilgore | N-substituted alpha-oxyacetamides and insect combating compositions |
-
0
- DE DENDAT102892D patent/DE102892C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426885A (en) * | 1942-10-09 | 1947-09-02 | Lowell B Kilgore | N-substituted alpha-oxyacetamides and insect combating compositions |
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