1213-06-5

Basic information

• Product Name: N,N-DIETHYL-4-SULFAMOYLBENZOIC ACID
• Synonyms: Ethebenecid;N, N-Diethyl-p-sulfamoylbenzoic acid;Urelim;Benzoic acid, 4-[(diethylamino)sulfonyl]-;Benzoic acid, p-(diethylsulfamoyl)-;Etamid;Ethebenecide;Benzoic acid, 4-((diethylamino)sulfonyl)- (9CI)
• CAS NO: 1213-06-5
• Molecular Formula: C₁₁H₁₅NO₄S
• Molecular Weight: 257.3061
• EINECS: 214-925-4
• Mol File: 1213-06-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 192-194° (with turbidity)
• Boiling Point: 416.5 °C at 760 mmHg
• Flash Point: 205.7 °C
• Appearance: /
• Density: 1.283 g/cm³
• Vapor Pressure: 1.11E-07mmHg at 25°C
• PKA: 3.59±0.10(Predicted)
• CAS DataBase Reference: N,N-DIETHYL-4-SULFAMOYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIETHYL-4-SULFAMOYLBENZOIC ACID(1213-06-5)
• EPA Substance Registry System: N,N-DIETHYL-4-SULFAMOYLBENZOIC ACID(1213-06-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1213-06-5(Hazardous Substances Data)

Usage

Description

N,N-Diethyl-4-sulfamoylbenzoic acid is a sulfonamide derivative, characterized by the presence of a sulfonyl group attached to a benzene ring, with two ethyl groups and a sulfamoyl group also attached to the ring. It is a white to off-white crystalline solid that exhibits stability under normal conditions. N,N-DIETHYL-4-SULFAMOYLBENZOIC ACID is recognized for its role as an intermediate in the synthesis of pharmaceuticals, leveraging its sulfonamide functionality, which is known for its biological activity and therapeutic potential.

Uses

Used in Pharmaceutical Synthesis:
N,N-Diethyl-4-sulfamoylbenzoic acid is used as an intermediate in the synthesis of various pharmaceuticals, particularly diuretic drugs. Its sulfonamide functionality contributes to the biological activity and therapeutic potential of the final drug products, making it a valuable component in medicinal chemistry.
Used in Diuretic Drug Development:
In the pharmaceutical industry, N,N-Diethyl-4-sulfamoylbenzoic acid is utilized as a key component in the development of diuretic medications. N,N-DIETHYL-4-SULFAMOYLBENZOIC ACID's structure and properties allow it to contribute to the efficacy of these drugs, which are designed to increase the amount of urine produced and excreted, thereby helping to remove excess water and salt from the body. This application is crucial for treating conditions like hypertension, heart failure, and kidney diseases.

InChI:InChI=1/C11H15NO4S/c1-3-12(4-2)17(15,16)10-7-5-9(6-8-10)11(13)14/h5-8H,3-4H2,1-2H3,(H,13,14)/p-1

Upstream product

• 10130-89-9 p-carboxyphenylsulfonyl chloride 
• 109-89-7 diethylamine 

Downstream Products

• 1093988-02-3 4-{[2-({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}acetyl)hydrazino]carbonyl}-N,N-diethylbenzenesulfonamide 
• 1070792-19-6 N-[4-(4-cyanophenyl)thiazol-2-yl]-4-diethylaminosulfonylbenzamide 
• 96134-63-3 N,N-Diethyl-4-(5-ethyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 96134-62-2 N,N-Diethyl-4-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 96134-61-1 N,N-Diethyl-4-[1,3,4]oxadiazol-2-yl-benzenesulfonamide 
• 96134-64-4 N,N-Diethyl-4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-benzenesulfonamide 
• 53554-97-5 4-<(Diethylamino)sulfonyl>benzoic Acid Hydrazide 
• 552305-10-9 2-(4'-diethylsulfonamide phenyl)-1,3,4-oxadiazolin-5-thione 
• 951213-47-1 methyl 4-(N,N-diethylsulfamoyl)benzoate 
• 5325-05-3 4-<(Diethylamino)sulfonyl>benzoic Acid Ethyl Ester 
• 29171-71-9 4-(N,N-diethylsulfamoyl)benzoyl chloride 

Relevant articles and documents

Syntheses and biological activity of 2-(4'-diethylsulfonamide phenyl)-4-substituted aminomethyl-1,3,4-oxadiazolin-5-thiones

4-(Chlorosulfonyl) benzoic acid was condensed with diethyl amine to afford 4-(diethylsulfamoyl) benzoic acid 1 which was esterified to obtain methyl ester 2. The condensation of compound 2 with hydrazine hydrate gave hydrazino derivative 3. This intermediate undergoes cyclization with carbon disulphide and potassium hydroxide to yield substituted 1,3,4-oxadiazolin-5-thione 4. Aminomethylation of 4 using different amines furnished 4-substituted aminomethyl-2-(4'-diethylsulphonamide phenyl)-1,3,4-oxadiazolin-5-thiones 5a-e. The structure of the newly synthesized compounds have been established by analytical and spectral data. These compounds have also been screened for their biological activity.

Factors Which Influence the Formation of Oxadiazoles from Anthranilhydrazides and Other Benzoylhydrazines

The cyclization of o-aminobenzoylhydrazine (1a) and its 5-methyl derivative 1b with four equivalents and with one equivalent of triethyl orthoacetate (TEOA) was studied. 3-Amino-2-methyl-4(3H)-quinazolinone (2a), 3,4-dihydro-2-methyl-5H-1,3,4-benzotriazepin-5-one (3a) and an imino ether derivative of 2a, N-ethanimidic acid ethyl ester (4a) were obtained from the reaction of 1a with four equivalents of TEOA.These results were compared with those of Merour who isolated 2a and 3a using the same conditions.When 1a was treated with one equivalent of TEOA, 2a, 3a, and a new product, 2-(5-methyl-1,3,4-oxadiazol-2-yl)benzenamine (5a) were produced, and 4a was not.Similar results were obtained with the reactions of 1b with TEOA.Authentic samples of oxadiazoles 5a and b were prepared by alternate routes.Novel acid-catalyzed rearrangements of benzotriazepinones 3a and b, to mixtures of aminoquinazolinones 2a and b and oxadiazoles 5a and b, respectively, were found.The different relative amounts of aminoquinazolinones 2 and oxadiazoles 5 which were produced from these rearrangements allowed us to choose between two potential mechanism for these interesting rearrangements.Treatment of 5-nitrobenzoylhydrazine (37) with four equivalents of TEOA gave three products which were characterized, but did not lead to benzotriazepinone formation.