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TitleA cost-effective one pot acylation process of aromatic amines for preparation of various amides used in pharmaceuticals, agrochemicals, cosmetic and flavouring agents
Knowhow is available forA general methodology for a cost-effective, efficient and environmental friendly acylation process for the preparation of amides from aromatic or aliphatic amines using non-toxic, harmless, cheap and easily available acylating agent such as DEM
SummaryAmide formation is a commonly used and an important reaction in organic chemistry. Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid found in fruits like grapes, pineapples and strawberries. Although DEM is extensively used in the famous name reaction, "Malonic Ester Synthesis (MES)", but the application of DEM for "Malonic Ester Amide Synthesis (MEAS)" never emerged as general process for synthesis of amides. CSIR-NCL has developed an innovative process which is an improved, cost-effective and efficient catalytic decarboxylative acylation of aromatic/heteroaromatic, primary /secondary amines using malonic ester to obtain corresponding amides in good yield with high degree of purity.
Furthermore the catalytic decarboxylation of the intermediate may be self- catalyzed i.e. the decarboxylation may be effected by the amine substrate used in the reaction, preferably when the substrate is hetero-aromatic amine. In addition, the present invention also provides MEAS methodology for the preparation of polyamide. It offers a suitable alternative in industries for easy preparation of various aromatic amines to diverse amides such as carbon homologated amides, N-phenylacetamide, N-phenylpropionamide to name a few.
The process gives easy access to amides with odd/even chain lengths and array of substituents on the alkyl/aryl part. The synthesis of odd chain lengths is noteworthy and important because most of the naturally occurring long chain alcohols/acids (which are commonly used as starting materials in the prior art) have even chain lengths.
- Suitable alternative in industries for easy preparation, of various aromatic amines to diverse amides
- Preparation of various amines using DEM for pharmaceuticals, agrochemicals and poly amides
- DEM is a common ingredient of perfumes, artificial flavourings and extensively used in the famous name reaction, "Malonic Ester Synthesis (MES)"
- DEM is used in the preparation of CNS depressant drugs barbiturates and important vitamins like vitamin Bi & B6.
Advantages- Cost effective methodology
- Environmental friendly and efficient, no use of highly corrosive and toxic reagents, harmful or banned chemicals such as acyl chlorides, acetic anhydride, organic bases as well as expensive peptide coupling reagents or metal catalysts
- Avoids complex reaction mixture consisting of undesired side products, which otherwise complicate, downstream processing and extraction of compound of interest
- Good yield with a high degree of purity of specific product desired
- Minimal waste generation in chemical process
- Synthesis of odd chain lengths is significant as the starting materials in the prior art) have even chain lengths
- Easy access to amides with odd/even chain lengths and array of substituents on the alkyl/aryl part
- Obviates the lengthy and cumbersome process presently being used, by providing a simple, one pot process

Knowhow is listed under following categories

Knowhow from
Scientific/ engineering subject areas Chemical sciences & engineering ; Others
Investor interest categories Materials Technology including Nanotechnology
Industries Organic Chemicals, Fine Chemicals, Intermediates, Feedstocks
Customer categories and nature of business Businesses and other industries (B2B)
Technology readiness levels TRL C: Prototype developed and tested; technology demonstrated at pilot scale

Year of development
Whether patents are part of this offering ?Yes

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Database reference

Database record number 20140423123226
Date of upload 23 / Apr / 2014
Date of update 2 / May / 2014
URL to site when communicating about this knowhow http://nclinnovations.org/khdb/viewrecord.php?recordno=20140423123226
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