ChemicalBook CAS DataBase List Glibenclamide

Glibenclamide synthesis

11synthesis methods

Product Name:Glibenclamide
CAS Number:10238-21-8
Molecular formula:C23H28ClN3O5S
Molecular Weight:494

Glyburide, 1-[4-[2-(5-chloro-2-methoxybenzamido)ethyl]-phenylsulfonyl]-3- cyclohexylurea (26.2.11), is a second-generation drug that differs from those described above in that it has a more complex structure in the sulfonylamide region of the molecule into which an additional pharmacophore group is added. It is synthesized from 2-methoxy-5-chlorobenzoic acid chloride, which is transformed into an amide 26.2.9 by reacting it with 2-phenylethylamine. This undergoes subsequent sulfonylchlorination by chlorosulfonic acid, and then amination by ammonia, which gives sulfonamide 26.2.10. The resulting sulfonamide is reacted with cylclohexylisocyanate to give the desired glyburide (26.2.11).

4-(2-(5-Chloro-2-methoxybenzamido)ethyl)benzenesulfamide

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Yield:10238-21-8 4.49 g

Reaction Conditions:

with 18-crown-6 ether;potassium tert-butylate in N,N-dimethyl-formamide at 0 - 5; for 6 h;Reflux;

Steps:

1.5 Addition:

3.69 g (10 mmol) of Compound IV was dissolved in 50 mL of DMF.1.34 g (12 mmol) of potassium tert-butoxide and 0.8 g (3 mmol) of 18-crown-6 ether are added;Cyclohexyl isocyanate is dissolved in DMF,Formulated as a 1mol/L solution13 mL of this solution was added dropwise to the solution of compound IV at 0-5°C.After it is completely added,Warming to reflux reaction for 6h,Pour into 1N dilute hydrochloric acid at 0-5°C,Filtering,Vacuum drying4.49 g (9.1 mmol) of glyburide was obtained.

References:

CN107879955,2018,A Location in patent:Paragraph 0052

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