Tolbutamide synthesis
BP607P Medicinal Chemistry III Practical : I Preparation of drugs Sulphanilamide * 7-Hydroxy, 4-methyl coumarin * Chlorobutanol * Triphenyl imidazole * Tolbutamide * Hexamine II Assay of drugs Isonicotinic acid hydrazide * Chloroquine * Metronidazole * Dapsone * Chlorpheniramine maleate * Benzyl penicillin III Microwave irradiation technique Synthesis of Phenytoin by Microwave * Synthesis of Aspirin by Microwave IV Drawing structures and reactions using chem draw®
Aim
To prepare and submit tolbutamide from p-toluene sulfonamide and calculate its percentage yield.
Principle:
The synthesis of tolbutamide involves addition reaction of p-toluene sulfonamide and butyl isocyanate in the presence of triethylamine and tetrahydrofuran.
Reaction:
Chemical Required:
p-Toluene Sulfonamide – 1 g
Butyl isocyanate – 1 g
Triethylamine – 1.2 ml
Tetrahydrofuran – 10 ml
Procedure:
About N-butyl isocyanate (1m mol) and triethylamine (1.2m mol) in a round bottom flask containing 10 ml of tetrahydrofuran, kept in an ice bath.
To the above mixture P-toluene sulfonamide (1m mol) was added drop wise at 0oc.
After completing the addition, the temperature was suddenly raised to 35-45oC and stirred for 3-4 Hrs.
Then the solution was filtered.
The product was separated and dried. Then it was recrystalised by using Diethyl ether.
Melting Point: 128oC to 129oC
Use:
Anti-diabetic
Report:
Tolbutamide was Prepared and submitted. Report the Following
Theoretical Yield:
Practical Yield:
Percentage Yield:
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