Synthesis of amides from acid and amine using - Journal of Current ...

Journal of Current Pharmaceutical Research 2012; 10 (1): 22-24
ISSN 0976-3171
JCPR 2012;10 (1): 22-24
© 2010 Medipoeia
Received 15-9-2012
Revised: 18-9-2012
Accepted: 19-9-2012
Synthesis of amides from acid and amine using
coupling reagents
Prasad B. Sambarkar*, Anand C. Patil
ABSTRACT
Objective: This paper describes the synthesis of amide using isovaleric acid and Aniline using
EDCI and HOBT.Solvent used for this reaction was dimethyl formamide (DMF). Reaction was
monitored using TLC. Solvent system used for TLC was 40% ethyl acetate + n-hexane the
recrystallization of product was carried out by using methanol. Percentage practical yield of
product is 62.6%. The I.R. of coupled product is 3244cm-1, 1654cm-1, 1599cm-1. LCMS of the
same compound showed 99.7% purity of the compound.
Prasad B. Sambarkar*,
Department of Chemistry, Deogiri
College Aurangabad, Maharashtra
India.
Anand C. Patil
Department of Chemistry Shri JJT
University, Jhunjhunu, Rajasthan
India.
Materials and methods: In R.B flask under N2 atmosphere, Isovaleric acid (50mg, 0.49mmole)
was dissolved in DMF (5ml). To this solution, EDCI (103.22mg, 0.54mmole) and HOBT (98mg,
0.59mmol) were added. The reaction mixture was stirred at room temp. For 15 mins. and then the
solution of aniline (54.70mg, 0.59 mmole) in DMF (5ml) was added to this reaction mixture.
Results: Theoretical yield was 86.76mg. Practical yield was 65.37mg. Percentage practical yield
was 74.91 %. The M.P. of coupled product was found to be 99-1000c. IR spectrum of coupled
product showed 3244cm-1, 1654cm-1, 1599cm-1. LCMS of the same compound showed 99.7%
purity of the compound.
Conclusion: By developing novel method of synthesis of amides, we have developed less solvent
consuming and hence economical method of amide formation.
Keywords: EDCI, HOBT, I.R., LCMS, DMF, Aniline, Isovaleric acid.
1. INTRODUCTION
There are different types of compounds which are found to be biological active. The
activity of these compounds can be attributed to the presence of various moieties like amides,
sulfonamides,thiols, amino compounds,steroids etc.
In this research project amide has been prepared using easily available carboxylic acid &
amine. The synthesis of amide make it possible to search . the amides are an important class of
compounds which are obtained by coupling of amine & acid using some coupling reagents like EDCI
,DCC etc. Here in this project we have used EDCI as coupling reagent, along with HOBt.
The basic building block of our body are proteins, called “first substance of life”.proteins
make up a large part the animal body , they hold it together & run it. They are found in all living
cells.they are principal material of skin, muscles, tendons, nerves, blood, enzymes, antibodies &many
harmones.
Chemically proteins are polymers, they are polyamides and monomers from which they are
derived are the α-amino acids. Taking into account of the above description the project was designed
to synthesize novel amide.
Correspondence:
Prasad .B. Sambarkar
Department of Chemistry,
Deogiri College Aurangabad-431 005
Maharashtra India.
Email:prasadsambarkar@gmail.com
EDCI
1-ethyl-3-(3-dimethylaminopropyl) carbodiimide
HOBT
1-Hydroxybenzotriazole

Journal of Current Pharmaceutical Research 2012; 10 (1): 22-24
2. METERIALS AND METHODS:
In R.B flask under N2 atmosphere, Isovaleric
acid(50mg,0.49mmole) was dissolved in DMF (5ml). To this
solution, EDCI (103.22mg, 0.54mmole) and HOBT (98mg,
0.59mmol) were added. The reaction mixture was stirred at room
temp. for 15 mins. and then the solution of aniline (54.70mg, 0.59
mmole) in DMF (5ml) was added to this reaction mixture.
The ethyl acetate layer was washed with 10% HCl
solution and two layers were separated. It was then washed with
10ml of brine solution. The ethyl acetate layer was dried over
anhydrous sodium sulfate and evaporated in vacuum to give
coupled compound. It yielded crude product (67mg). It was
recrystallized by methanol. Its purity was determined by TLC. The
I.R. of coupled product is 3244cm-1,1654cm-1, 1599cm-1. LCMS
of the same compound showed 99.7% purity of the compound.
+
EDCI/HOBT
3. RESULTS AND DISCUSSIONS:
Theoretical yield was 86.76mg.
Practical yield was 65.37mg.
Percentage practical yield was 74.91 %.
The M.P. of coupled product was found to be 99-1000c.
IR spectrum of coupled product showed 3244cm-1,1654cm-1,
1599cm-1.
LCMS of the same compound showed 99.7% purity of the
compound.
Reaction was monitored using TLC. To this reaction
mixture, 20 ml ethyl acetate was added. It was washed with 10%
aqueous solution. of sodium bicarbonate. Two layers were
separated properly.
4. CONCLUSION:
By developing novel method of synthesis of amides, we
have developed less solvent consuming and hence economical
method of amide formation.

Journal of Current Pharmaceutical Research 2012; 10 (1): 22-24
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