UC206L

Ankur Bhaumik
18895

Lab -4
Synthesis of 3,5- Dimethylpyrazole

Aim- To synthesize 3,5- Dimethylpyrazole, a nitrogen containing heterocyclic

compound.

Principle-
Heterocyclic compounds are cyclic organic compounds containing carbon and
other heteroatoms such as oxygen, nitrogen, or sulphur. The ring may be
aromatic or non-aromatic. They are quite commonly encountered in nature.
They are of immense importance in medicinal chemistry and in agrochemistry
and polymer chemistry.

General reaction

Acetyl Acetone Hydrazine hydrate 3,5- Dimethylpyrazole

Mechanism
Calculation

Compound Mol. Wt. (g/mol) Density (g/mL) Amount (mL) Equivalent mol
Acetylacetone 100.12 0.975 10 0.0974 0.0974
Hydrazine hydrate 50.061 1.03 8 0.1646 0.1646
H O 18 1 50 - -
2

Theoretically- Acetylacetone and hydrazine hydrate should be taken in a 1:1

ratio but in the experiment it was taken in a 1:1.67 ratio to increase the rate of
the reaction.

Procedure

1. In a 100 mL RB 10 ml of acetylacetone) and 50 ml of water was taken.

2. The reaction mixture was heated at 40 °C
3. 8 ml of hydrazine hydrate was slowly added into the reaction mixture and
temperature was maintained at 40 °C to 50 °C
4. After the addition was completed, a crystalline solid was precipitated out.
5. Stirring was continued further for 10-15 min. After the RB was put in ice-
bath.
 6. The solid was filtered, dried in air, and weighed.
7. Yield was calculated.
8. Melting point is measured.

Melting Point

Melting point observed- 106˚C to 108˚C

Yield Calculation
1 𝑚𝑜𝑙𝑒 𝑜𝑓 ℎ𝑦𝑑𝑟𝑎𝑧𝑖𝑛𝑒 𝑟𝑒𝑎𝑐𝑡𝑠 𝑤𝑖𝑡ℎ 1 𝑚𝑜𝑙𝑒 𝑜𝑓 𝑎𝑐𝑒𝑡𝑦𝑙𝑎𝑐𝑒𝑡𝑜𝑛𝑒.
𝑁𝑜𝑤, 𝑙𝑒𝑠𝑠𝑒𝑟 𝑎𝑚𝑜𝑢𝑛𝑡 𝑜𝑓 𝑎𝑐𝑒𝑡𝑦𝑙𝑎𝑐𝑒𝑡𝑜𝑛𝑒 𝑖𝑠 𝑝𝑟𝑒𝑠𝑒𝑛𝑡 𝑠𝑜, 𝑖𝑡 𝑖𝑠 𝑡ℎ𝑒 𝑙𝑖𝑚𝑖𝑡𝑖𝑛𝑔 𝑟𝑒𝑎𝑔𝑒𝑛𝑡.

𝐸𝑥𝑝𝑒𝑐𝑡𝑒𝑑 𝑛𝑜. 𝑜𝑓 𝑚𝑜𝑙𝑒𝑠 𝑜𝑓 3,5 − 𝐷𝑖𝑚𝑒𝑡ℎ𝑦𝑙𝑝𝑦𝑟𝑎𝑧𝑜𝑙𝑒 = 0.0974

𝑀𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 3,5 − 𝐷𝑖𝑚𝑒𝑡ℎ𝑦𝑙𝑝𝑦𝑟𝑎𝑧𝑜𝑙𝑒 = 96 𝑔/𝑚𝑜𝑙𝑒

𝐸𝑥𝑝𝑒𝑐𝑡𝑒𝑑 𝑤𝑒𝑖𝑔ℎ𝑡 𝑜𝑓 3,5 − 𝐷𝑖𝑚𝑒𝑡ℎ𝑦𝑙𝑝𝑦𝑟𝑎𝑧𝑜𝑙𝑒 = 0.0974 𝑚𝑜𝑙𝑒 × 96 𝑔/𝑚𝑜𝑙𝑒 = 9.35 𝑔
𝑂𝑏𝑡𝑎𝑖𝑛𝑒𝑑 𝑤𝑒𝑖𝑔ℎ𝑡 𝑜𝑓 3,5 − 𝐷𝑖𝑚𝑒𝑡ℎ𝑦𝑙𝑝𝑦𝑟𝑎𝑧𝑜𝑙𝑒 = 7.012 𝑔

𝑂𝑏𝑡𝑎𝑖𝑛𝑒𝑑 𝑤𝑒𝑖𝑔ℎ𝑡 7.012

𝑆𝑜, 𝑌𝑖𝑒𝑙𝑑 = × 100% = × 100% = 74.99%
𝐸𝑥𝑝𝑒𝑐𝑡𝑒𝑑 𝑤𝑒𝑖𝑔ℎ𝑡 9.35

Conclusion

• 3,5-Dimethylpyrazole was synthesized with 74.99% yield.

• Acetylacetone is the limiting reagent.
• Observed melting point for the synthesized compound is 106˚C to 108˚C.