ChemicalBook CAS DataBase List Bumetanide

Bumetanide synthesis

3synthesis methods

Product Name:Bumetanide
CAS Number:28395-03-1
Molecular formula:C17H20N2O5S
Molecular Weight:364.42

Bumetanide, 3-butylamino-4-phenoxy-5-sulfamoylbenzoic acid (21.4.6), is synthesized from 4-chlorobenzoic acid. In the first stage of synthesis, it undergoes sulfonylchlorination by chlorosulfonic acid, forming 4-chloro-3-chlorosulfonylbenzoic acid (21.4.1), which is further nitrated with nitric acid to 4-chloro-3-chlorosulfonyl-5-nitrobenzoic acid (21.4.2). Reacting this with ammonia gives 5-aminosulfonyl-4-chloro-3-nitrobenzoic acid (21.4.3), which when reacted with sodium phenolate is transformed into 5-amino-sulfonyl-3-nitro-5-phenoxybenzoid acid (21.4.4). Reduction of the nitro group in this product by hydrogen using a palladium on carbon catalyst gives 3-amino-5-aminosulfonyl- 5-phenoxybenzoic acid (21.4.5). Finally, reacting this with butyl alcohol in the presence of sulfuric acid gives the desired bumetanide (21.4.6).

3-amino-5-(aminosulphonyl)-4-phenoxybenzoic acid

28328-54-3
67 suppliers
$190.00/y0000310

71-36-3 Synthesis

71-36-3
1019 suppliers
$14.00/25mL

28395-03-1
287 suppliers
$35.00/500mg

Yield:28395-03-1 95.8%

Reaction Conditions:

with iron(III) chloride;boron trifluoride diethyl etherate at 20; for 6 h;Reagent/catalyst;

Steps:

4 Example 4
0.1 mol of 3-amino-4-phenoxy-5-sulfonamide benzoic acid was added to the reaction flask, and then 500 ml of n-butanol was added and stirred at room temperature. To the reaction flask, 5 mmol of boron trifluoride diethyl ether and 5mmol ferric chloride, the reaction 6 hours until the reaction is complete, stop stirring,After most of the n-butanol was distilled off from the reaction mixture, 200 ml of 2 M sodium hydroxide solution and 100 ml were addedEthanol was heated to reflux for 30 minutes, then add concentrated hydrochloric acid to adjust the pH to 8-8.2, cooled, standing, suction filtration, filtration, the filter cake plus water and heated to dissolve, add a small amount of activated carbon decolorization,After filtration, the sodium salt was precipitated by cooling and after filtration, 300 ml of water was added into the solution to dissolve it,Then add concentrated hydrochloric acid to pH2-3, cooling, suction filtration, washing and drying to obtain a pure product of bumetanide,Yield 95.8%, purity 99.4%.

References:

Zaozhuang Run'an Pharmaceutical New Materials Co., Ltd.;Zhang Fengzhi CN106748906, 2017, A Location in patent:Paragraph 0015; 0016; 0017; 0018; 0019

FullText

butyl 3-aminosulphonyl-5-butylamino-4-phenoxybenzoate

32643-00-8
57 suppliers
$495.77/5MG

28395-03-1
287 suppliers
$35.00/500mg

References

Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-, methyl ester

28510-66-9
1 suppliers
inquiry

28395-03-1
287 suppliers
$35.00/500mg

References

Bumetanide Related Search:

4-Dimethylaminobenzoic acid Benzoic acid 4-Aminobenzoic acid 4-Methoxybenzoic acid Bufexamac TOLBUTAMIDE Estradiol benzoate 3-Amino-4-hydroxybenzoic acid (4-PHENOXYPHENYL)METHANOL Butylamine