In the literature only a few "ortho-amides", of the type R - C(NR'2)3, are mentioned. Giacalone prepared trianilinomethane by heating aniline and ethyl orthoformate. In the same way Lewis and Post made derivatives of this compound, starting from the chloro-anilines. ... Zie: Summary

Wanmaker, Willem Lambertus

ARTS repository - University of Groningen

   University of GroningenGesubtitueerde formamidinen en trichlooraceetamidinenWanmaker, Willem LambertusIMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite fromit. Please check the document version below.Document VersionPublisher's PDF, also known as Version of recordPublication date:1949Link to publication in University of Groningen/UMCG research databaseCitation for published version (APA):Wanmaker, W. L. (1949). Gesubtitueerde formamidinen en trichlooraceetamidinen. Noordhoff Uitgevers.CopyrightOther than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of theauthor(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).The publication may also be distributed here under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license.More information can be found on the University of Groningen website: https://www.rug.nl/library/open-access/self-archiving-pure/taverne-amendment.Take-down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediatelyand investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons thenumber of authors shown on this cover page is limited to 10 maximum.Download date: 31-10-2023SUMMARY.In the literature only a few "ortho-amides", of the typeR - C(NR'z)3, aÍe mentioned. Giacalone prepared tr iani l ino-methane by heating aniline and ethyl orthoformate. In the sameway Lewis and Post made derivatives of this compound, startíngfrom the chloro-anilines.By repeating their work we were able to prove that the non-sub-stituted aromatic orthoamides do not exist, but that the reactionproducts are identical with already known diarylformamidines. Whenreacting with aniline, diethoxymethyl acetate and ethyl orthoacetatealso give rise to the formation of amidines. We succeeded insynthetizing an orthoamide from ethyl orthoformate and methyl-aniline (trimethylphenyl-aminomethane).Piperidine reacts at elevated temperature with ethyl orthocarbo-nate, orthotormate and orthoacetate, giving acylpiperidides andethylpiperidine.From ethyl orthoformate and some primary aromatic aminesseveral substituted diarylformamidines have been prepared.Further we studied the addition of basic compounds to trichloro-acetonitrile. The known addition of aliphatic amines was extendedto aromatic amines, in the presence of methanol or AlCl3.Addition of guanidine and derivatives yields N-trichloro-acet-imino-guanidines. We also prepared the addition-compounds ofacetamidine and N-phenyl-O-ethyl-isourea to trichloroacetonitrile.On page 58 an electronic interpretation of the addition-reactionsstudied is given. We assume that the nucleophilic addition startsat the carbon atom of the cyane group.Some of the new compounds have been tested on their bacterio-static activity. They have been found to be active, though too toxicfor chemotherapeutic application.

Dutch

Gesubtitueerde formamidinen en trichlooraceetamidinen

University of Groningen

   University of GroningenGesubtitueerde formamidinen en trichlooraceetamidinenWanmaker, Willem LambertusIMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite fromit. Please check the document version below.Document VersionPublisher's PDF, also known as Version of recordPublication date:1949Link to publication in University of Groningen/UMCG research databaseCitation for published version (APA):Wanmaker, W. L. (1949). Gesubtitueerde formamidinen en trichlooraceetamidinen. Groningen: NoordhoffUitgevers.CopyrightOther than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of theauthor(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).Take-down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediatelyand investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons thenumber of authors shown on this cover page is limited to 10 maximum.Download date: 12-11-2019SUMMARY.In the literature only a few "ortho-amides", of the typeR - C(NR'z)3, aÍe mentioned. Giacalone prepared tr iani l ino-methane by heating aniline and ethyl orthoformate. In the sameway Lewis and Post made derivatives of this compound, startíngfrom the chloro-anilines.By repeating their work we were able to prove that the non-sub-stituted aromatic orthoamides do not exist, but that the reactionproducts are identical with already known diarylformamidines. Whenreacting with aniline, diethoxymethyl acetate and ethyl orthoacetatealso give rise to the formation of amidines. We succeeded insynthetizing an orthoamide from ethyl orthoformate and methyl-aniline (trimethylphenyl-aminomethane).Piperidine reacts at elevated temperature with ethyl orthocarbo-nate, orthotormate and orthoacetate, giving acylpiperidides andethylpiperidine.From ethyl orthoformate and some primary aromatic aminesseveral substituted diarylformamidines have been prepared.Further we studied the addition of basic compounds to trichloro-acetonitrile. The known addition of aliphatic amines was extendedto aromatic amines, in the presence of methanol or AlCl3.Addition of guanidine and derivatives yields N-trichloro-acet-imino-guanidines. We also prepared the addition-compounds ofacetamidine and N-phenyl-O-ethyl-isourea to trichloroacetonitrile.On page 58 an electronic interpretation of the addition-reactionsstudied is given. We assume that the nucleophilic addition startsat the carbon atom of the cyane group.Some of the new compounds have been tested on their bacterio-static activity. They have been found to be active, though too toxicfor chemotherapeutic application.

NARCIS 

   University of GroningenGesubtitueerde formamidinen en trichlooraceetamidinenWanmaker, Willem LambertusIMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite fromit. Please check the document version below.Document VersionPublisher's PDF, also known as Version of recordPublication date:1949Link to publication in University of Groningen/UMCG research databaseCitation for published version (APA):Wanmaker, W. L. (1949). Gesubtitueerde formamidinen en trichlooraceetamidinen. Noordhoff Uitgevers.CopyrightOther than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of theauthor(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).The publication may also be distributed here under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license.More information can be found on the University of Groningen website: https://www.rug.nl/library/open-access/self-archiving-pure/taverne-amendment.Take-down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediatelyand investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons thenumber of authors shown on this cover page is limited to 10 maximum.Download date: 07-06-2022SUMMARY.In the literature only a few "ortho-amides", of the typeR - C(NR'z)3, aÍe mentioned. Giacalone prepared tr iani l ino-methane by heating aniline and ethyl orthoformate. In the sameway Lewis and Post made derivatives of this compound, startíngfrom the chloro-anilines.By repeating their work we were able to prove that the non-sub-stituted aromatic orthoamides do not exist, but that the reactionproducts are identical with already known diarylformamidines. Whenreacting with aniline, diethoxymethyl acetate and ethyl orthoacetatealso give rise to the formation of amidines. We succeeded insynthetizing an orthoamide from ethyl orthoformate and methyl-aniline (trimethylphenyl-aminomethane).Piperidine reacts at elevated temperature with ethyl orthocarbo-nate, orthotormate and orthoacetate, giving acylpiperidides andethylpiperidine.From ethyl orthoformate and some primary aromatic aminesseveral substituted diarylformamidines have been prepared.Further we studied the addition of basic compounds to trichloro-acetonitrile. The known addition of aliphatic amines was extendedto aromatic amines, in the presence of methanol or AlCl3.Addition of guanidine and derivatives yields N-trichloro-acet-imino-guanidines. We also prepared the addition-compounds ofacetamidine and N-phenyl-O-ethyl-isourea to trichloroacetonitrile.On page 58 an electronic interpretation of the addition-reactionsstudied is given. We assume that the nucleophilic addition startsat the carbon atom of the cyane group.Some of the new compounds have been tested on their bacterio-static activity. They have been found to be active, though too toxicfor chemotherapeutic application.

English

University of Groningen Research Database

  
 University of Groningen
Gesubtitueerde formamidinen en trichlooraceetamidinen
Wanmaker, Willem Lambertus
IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from
it. Please check the document version below.
Document Version
Publisher's PDF, also known as Version of record
Publication date:
1949
Link to publication in University of Groningen/UMCG research database
Citation for published version (APA):
Wanmaker, W. L. (1949). Gesubtitueerde formamidinen en trichlooraceetamidinen Groningen: Noordhoff
Uitgevers
Copyright
Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the
author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).
Take-down policy
If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately
and investigate your claim.
Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the
number of authors shown on this cover page is limited to 10 maximum.
Download date: 10-02-2018
SUMMARY.
In the literature only a few "ortho-amides", of the type
R - C(NR'z)3, aÍe mentioned. Giacalone prepared tr iani l ino-
methane by heating aniline and ethyl orthoformate. In the same
way Lewis and Post made derivatives of this compound, startíng
from the chloro-anilines.
By repeating their work we were able to prove that the non-sub-
stituted aromatic orthoamides do not exist, but that the reaction
products are identical with already known diarylformamidines. When
reacting with aniline, diethoxymethyl acetate and ethyl orthoacetate
also give rise to the formation of amidines. We succeeded in
synthetizing an orthoamide from ethyl orthoformate and methyl-
aniline (trimethylphenyl-aminomethane).
Piperidine reacts at elevated temperature with ethyl orthocarbo-
nate, orthotormate and orthoacetate, giving acylpiperidides and
ethylpiperidine.
From ethyl orthoformate and some primary aromatic amines
several substituted diarylformamidines have been prepared.
Further we studied the addition of basic compounds to trichloro-
acetonitrile. The known addition of aliphatic amines was extended
to aromatic amines, in the presence of methanol or AlCl3.
Addition of guanidine and derivatives yields N-trichloro-acet-
imino-guanidines. We also prepared the addition-compounds of
acetamidine and N-phenyl-O-ethyl-isourea to trichloroacetonitrile.
On page 58 an electronic interpretation of the addition-reactions
studied is given. We assume that the nucleophilic addition starts
at the carbon atom of the cyane group.
Some of the new compounds have been tested on their bacterio-
static activity. They have been found to be active, though too toxic
for chemotherapeutic application.


Gesubtitueerde formamidinen en trichlooraceetamidinen

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