Tolbutamide synthesis: Medicinal Chemistry Practical, Lab manual, PDF

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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®

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Aim

To prepare and submit tolbutamide from p-toluene sulfonamide and calculate its percentage yield.

Principle synthesis of tolbutamide pdf:

The synthesis of tolbutamide involves addition reaction of p-toluene sulfonamide and butyl isocyanate in the presence of triethylamine and tetrahydrofuran.

Reaction:

starting material for synthesis of tolbutamide:

p-Toluene Sulfonamide – 1 g
Butyl isocyanate – 1 g
Triethylamine – 1.2 ml
Tetrahydrofuran – 10 ml

synthesis of tolbutamide from toluene 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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Third Year B Pharm Notes, Syllabus, Books, PDF Subjectwise/Topicwise

T Y B Pharm Sem V	T Y B Pharm Sem VI
BP501T Medicinal Chemistry II Theory	BP601T Medicinal Chemistry III Theory
BP502T Industrial Pharmacy Theory	BP602T Pharmacology III Theory
BP503T Pharmacology II Theory	BP603T Herbal Drug Technology Theory
BP504T Pharmacognosy II Theory	BP604T Biopharmaceutics and Pharmacokinetics Theory
BP505T Pharmaceutical Jurisprudence Theory	BP605T Pharmaceutical Biotechnology – Theory
BP506P Industrial Pharmacy I Practical	BP606T Quality Assurance Theory
BP507P Pharmacology II Practical	BP607P Medicinal chemistry III Practical
BP508P Pharmacognosy II Practical	BP608P Pharmacology III Practical
	BP609P Herbal Drug Technology Practical

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Suggested readings

• Chlorobutanol Synthesis
• BP607P Medicinal Chemistry III Practical
• Benzoic acid from benzamide synthesis: Pharmaceutical Chemistry Practical
• 7-Hydroxy 4-methyl coumarin synthesis
• Synthesis of Sulphanilamide

synthesis of tolbutamide slideshare

tolbutamide mechanism of action

Sulfonylureas lower blood glucose in patients with NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor (receptor 1) on the beta cell. Sulfonylureas inhibit the ATP-potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin-containing granules by exocytosis, an effect similar to that of glucose.

sar of tolbutamide

• The benzene ring should contain one substituent, preferably in the para position. The substituents that seem to enhance hypoglycemic activity are methyl, amino, acetyl, chloro, bromo, methylthio, and trifluoromethyl groups.
• Compounds with p-(-b-arylcarboxamidoethyl) substituents (the second generation agents) are orders of magnitude better than the first generation agents. It is believed that this is because of a specific distance between the nitrogen atom of the substituent and the sulfonamide nitrogen atom.
• The group attached to the terminal nitrogen should be of certain size and should impart lipophilic properties to the molecule. The N-methyl are inactive, N-ethyl have low activity, while N-propyl to N-hexyl are most active. Activity is lost if N-substituent contains 12 or more carbons.

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