CH269090A - Process for the preparation of a new aldehyde derivative. - Google Patents
Process for the preparation of a new aldehyde derivative.Info
- Publication number
- CH269090A CH269090A CH269090DA CH269090A CH 269090 A CH269090 A CH 269090A CH 269090D A CH269090D A CH 269090DA CH 269090 A CH269090 A CH 269090A
- Authority
- CH
- Switzerland
- Prior art keywords
- acetylamino
- preparation
- benzoic acid
- soluble
- formaldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims description 4
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Verfahren zur Darstellung eines neuen</B> Aldehydderivates. Gegenstand der Erfindung ist ein Verfah ren zur Herstellung eines neuen Abkömm lings eines Aldehydes, welcher gute keim tötende Eigenschaften besitzt. Er soll als Desinfektionsmittel und in Form seiner löslichen Salze zur Bekämpfung von Infek tionskrankheiten verwendet werden. Das Verfahren ist dadurch gekennzeichnet, dass man p-Acetyl-amino-benzoesäure auf Formaldehyd einwirken lässt, wobei sich die p- (N-Oxymethyl-acetylamino) -benzoesäure bil det.
Der Formaldehyd kann beispielsweise einer in Gegenwart der p-Acetylamino-benzoe- säure Formaldehyd liefernden Verbindung, z. B. einem polymeren Formaldehyd (Trioxy- methylen, Paraformaldehyd usw.) entstam men.
<I>Beispiel:</I> 1,8 g p- Acetylamino-benzoesäure, 0,8 cm3 40 %ige Formaldehydlösung und 5 cm3 2n- Diäthanolaminlösung werden gemischt und unter Schütteln bis zur klaren Lösung auf 80-9O0 <B>C</B> erwärmt.
Die heisse Lösung wird filtriert und in noch heissem Zustande auf ein pH von 4-5 eingestellt, worauf sich die p-(N-Oxymethyl-acetylamino)-benzoesäure als feines, weisses Kristallpulver abscheidet. Aus- beute: 1,5 g, entsprechend 72% der Theorie.
Die neue Karbonsäure ist in Alkalien und in Lösungen von Aminen leicht löslich, wenig löslich in Alkohol und schwer löslich in Was ser, Äther, Chloroform und Benzol. Sie besitzt schon bei Zimmertemperatur grosse Neigung, sich zu zersetzen. Bei höherer Temperatur erfolgt diese Umwandlung so rasch, dass der Schmelzpunkt der besehriebe- n.en Säure nicht ermittelt werden kann. Beständig sind dagegen die Salze der neuen Säure. Ihre wässrigen Lösungen reagie ren nahezu neutral und sind für Injektionen vorzüglich geeignet.
Die gebildete neue Karbonsäure lässt sich auch in Form ihrer Salze, z. B. des Natriums, Kalziums, oder als Salze von Aminen, wie Diäthylamin, Diäthanolamin, Morpholin, iso lieren. Zu diesem Zweck kann man beim Ar beiten gemäss dem Beispiel das Ansäuern des Reaktionsgemisches unterlassen; das dem ver wendeten alkalischen Kondensationsmittel ent sprechende Salz wird dann direkt und in nahezu quantitativer Ausbeute erhalten.
<B> Process for the preparation of a new </B> aldehyde derivative. The invention relates to a method for producing a new descendant of an aldehyde which has good germicidal properties. It should be used as a disinfectant and in the form of its soluble salts to combat infectious diseases. The process is characterized in that p-acetylamino-benzoic acid is allowed to act on formaldehyde, p- (N-oxymethyl-acetylamino) -benzoic acid being formed.
The formaldehyde can, for example, be a compound which yields formaldehyde in the presence of p-acetylamino-benzoic acid, e.g. B. a polymeric formaldehyde (trioxymethylene, paraformaldehyde, etc.) originates.
<I> Example: </I> 1.8 g of p-acetylamino-benzoic acid, 0.8 cm3 of 40% formaldehyde solution and 5 cm3 of 2N diethanolamine solution are mixed and brought to 80-90 ° C. with shaking until the solution is clear </B> heated.
The hot solution is filtered and adjusted to a pH of 4-5 while it is still hot, whereupon the p- (N-oxymethyl-acetylamino) -benzoic acid separates out as a fine, white crystal powder. Yield: 1.5 g, corresponding to 72% of theory.
The new carboxylic acid is easily soluble in alkalis and in solutions of amines, slightly soluble in alcohol and sparingly soluble in water, ether, chloroform and benzene. Even at room temperature it has a great tendency to decompose. At a higher temperature, this conversion takes place so quickly that the melting point of the particular acid cannot be determined. In contrast, the salts of the new acid are stable. Your aqueous solutions react almost neutrally and are ideally suited for injections.
The new carboxylic acid formed can also be in the form of its salts, e.g. B. of sodium, calcium, or as salts of amines such as diethylamine, diethanolamine, morpholine, iso lieren. For this purpose you can refrain from acidifying the reaction mixture when working according to the example; the salt corresponding to the alkaline condensing agent used is then obtained directly and in almost quantitative yield.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH269090T | 1948-05-20 | ||
| CH266516T | 1948-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH269090A true CH269090A (en) | 1950-06-15 |
Family
ID=25730897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH269090D CH269090A (en) | 1948-05-20 | 1948-05-20 | Process for the preparation of a new aldehyde derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH269090A (en) |
-
1948
- 1948-05-20 CH CH269090D patent/CH269090A/en unknown
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