3,5 Dimethylpyrazole
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ScribdTranslationsSalcedo Salas Adyanni Montserrat Group 1501 Drug Synthesis and Materials
primas II
3,5-Dimethylpyrazole
Study Guide
Azoles-1,2
They are five-membered aromatic heterocycles that contain an atom of
nitrogen as well as another heteroatom that can be sulfur, oxygen or
nitrogen.
Examples:
Pyrazoles: It is a weakly basic heterocycle that is protonated by reaction.
with many acids. As an acid, it is stronger than pyrrole, due to the
electron acceptor effect of N-azolic, capable of forming salts with ions
metallic.
Basicity of pyrazoles: The presence of the two neighboring nitrogens in the
Pyrazole reduces the basicity of the basic nitrogen (C=N) as occurs in the cases
of hydrazine and hydroxylamine (pKa (NH3)= 9.3; pKa (NH2NH2)= 7.9; pKa (NH2OH)=
5.8). For them, pyrazole (pKa = 2.5) is less basic than imidazole (pKa = 7.1).
Reactivity: The pyrazole group is a very reactive group that has the ability to
coordinate with transition metals and metalloids. It is a potentially ligand.
bidentate through coordination with its two nitrogens. Its greater or lesser
Nucleophilicity depends on its substituents. This group can act as a ligand.
neutral or anionic.
Methods for obtaining pyrazoles
a) Pechmann's Pyrazole Synthesis: It is a classic method in which
synthesize pyrazole from the dipolar cycloaddition of acetylene and
diazomethane.
b) Reaction between hydrazines and 1,3-difunctional compounds.
c) 1,3-dipolar cycloadditions.
How many products are obtained with asymmetric hydrazines?
Two products are formed since it is an asymmetric starting compound.
forman pirazoles isomers.
Spectroscopic signals (IR, NMR) of reactants and products.
2.3
11.98
11.98 5.73
2.3
IR spectrum
C=O Stretch: 1680 – 1630 cm -1
N-H Tension: Between 3350 and 3180 cm -1
Questionnaire
1) Indicate the raw materials used in the various syntheses of
pirazoles
Hydroxylamine
Hydrazine
Monosubstituted hydrazine 1,3-dicarbonyl
Cetoxime
Hydrozone
Alpha, beta olefinic compound
Alpha, beta acetylenic compound
2) Explain the mechanism of the proposed reaction.
By having a pair of electrons, hydrazine acts as a nucleophile and attacks.
the carbonyl group of the ketone and how two nitrogens are found and
two carbonyl groups, a five-membered ring is formed with two
nitrogen heteroatoms.
3) Mention the type of precautions that should be taken when using the
supplies required in the synthesis of 3,5-dimethylpyrazole
Hydrazine: It has a very strong and penetrating odor, it is also a very
strong reducing agent. The temperature must be controlled as
There may be a projection during the mixing of the reactants.
4) How is hydrazine released from the phosphate group so that it
does it act as a nucleophile?
It is released through the reaction of potassium acetate in water. It
heat to boiling, cool down and add alcohol. It is filtered under vacuum and the
filtration is free hydrazine.
If you did not have the solvent that the technician indicated for extraction of your
product What would be your criteria for choosing another one?
The solubility of 3,5-dimethylpyrazole in solvents is greater in ether.
oil so we could use hexane or toluene due to the
similar polarity to petroleum ether.
6) What range in the determination of the melting point of your product
should I accept?
Approximately ± 5°C
7) Indicate the characteristic absorption frequencies in the spectrum of
IR for carbonyl and amine groups
C=O: 1680 – 1630 cm -1
N-H: Between 3350 and 3180 cm -1
8) What techniques can you use to verify the purity of your
product?
Melting point primarily, but it could also be demonstrated
through an IR spectrum
9) Locate in the NMR spectrum the region where they appear
protons of the methyl groups and the proton of the carbon in position four
This response is found at the top when interpreting the
spectrum
10) Sodium dipyrone is a widely used analgesic in the country.
developed formula
minimum, c) molecular mass.
Minimum formula: C13H16N3O4SNa
333.34 g/mol
References:
Vogel, Textbook of Practical Organic Chemistry. 5th edition. New York.
Longman; 1989.
Gonzalez, C. Cornago M., Heterocyclic Chemistry. 1st edition. Madrid.
National University of Distance Education; 2015.
