94-19-9

Basic information

• Product Name: 4-AMINO-N-(5-ETHYL-[1,3,4]THIADIAZOL-2-YL)-BENZENESULFONAMIDE
• Synonyms: ethazole(pharmaceutical);globucid;globucin;globuzid;n-(5-ethyl-1,3,4-thiadiazol-2-yl)-sulfanilamid;n-(5-ethyl-1,3,4-thiadiazol-2-yl)sulfanilamide;setd;sethadil
• CAS NO: 94-19-9
• Molecular Formula: C₁₀H₁₂N₄O₂S₂
• Molecular Weight: 284.36
• EINECS: 202-312-4
• Mol File: 94-19-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 185.5-186.0°
• Boiling Point: 508.5°C at 760 mmHg
• Flash Point: 261.3°C
• Appearance: /
• Density: 1.3410 (rough estimate)
• Vapor Pressure: 1.85E-10mmHg at 25°C
• Refractive Index: 1.6440 (estimate)
• PKA: pKa 5.36(H2O t = 37) (Uncertain)
• Water Solubility: 215mg/L(20 oC)
• CAS DataBase Reference: 4-AMINO-N-(5-ETHYL-[1,3,4]THIADIAZOL-2-YL)-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N-(5-ETHYL-[1,3,4]THIADIAZOL-2-YL)-BENZENESULFONAMIDE(94-19-9)
• EPA Substance Registry System: 4-AMINO-N-(5-ETHYL-[1,3,4]THIADIAZOL-2-YL)-BENZENESULFONAMIDE(94-19-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 94-19-9(Hazardous Substances Data)

Usage

Originator

Sul-Spansion,SKF,US,1956

Manufacturing Process

0.163 mol of 2-amino-5-ethyl-1,3,4-thiadiazole was covered with 43 parts of anhydrous pyridine. To the mixture was added 50 parts (0.214 mol) of pacetylaminobenzenesulfonyl chloride with vigorous shaking at 50°C to 60°C. The reaction mixture was then heated to 125°C. When the mixture had cooled somewhat it was placed in a Claisen flask and 27.6 parts (0.69 mol) of sodium hydroxide dissolved in 110 parts of water was added through a dropping funnel while distilling off a mixture of pyridine and water. The distillation was stopped when the temperature reached 100°C and the residual liquor in the flask heated at 95°C for 30 minutes.The reaction mixture was then poured into 1,650 parts of hot water, the pH adjusted to 8 to 9, decolorizing charcoal was added and the whole was heated on the steam for 15 minutes. The charcoal was filtered off and the hot filtrate neutralized and cooled. The 2-(sulfanilamido)-5-ethyl-1,3,4-thiadiazole was purified by repeated crystallization from boiling water.

Therapeutic Function

Antibacterial

InChI:InChI=1/C10H12N4O2S2/c1-2-9-12-13-10(17-9)14-18(15,16)8-5-3-7(11)4-6-8/h3-6H,2,11H2,1H3,(H,13,14)

Upstream product

• 76170-72-4 2-(4-Nitrobenzenesulfonamido)-5-ethyl-1,3,4-thiadiazole 
• 1037-51-0 N-(4-(N-(5-ethyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 121-61-9 p-acetylaminobenzenesulfonamide 
• 100-05-0 4-nitrobenzenediazonium chloride 

Downstream Products

• 109698-58-0 4-acetylamino-2-hydroxy-benzoic acid-[4-(5-ethyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-anilide] 
• 109588-73-0 4-amino-2-hydroxy-benzoic acid-[4-(5-ethyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-anilide] 
• 104912-11-0 acetyl-(ethyl-[1,3,4]thiadiazol-2-yl)-sulfanilyl-amine 
• 132777-51-6 N-(2,4-dinitro-phenyl)-sulfanilic acid-(5-ethyl-[1,3,4]thiadiazol-2-ylamide) 
• 15018-98-1 4-amino-3,5-dibromo-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide 
• 41334-31-0 N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-4-[(2,4,6-trioxo-tetrahydro-pyrimidin-5-ylidene)-hydrazino]-benzenesulfonamide 
• 41334-32-1 4-[(4,6-dioxo-2-thioxo-tetrahydro-pyrimidin-5-ylidene)-hydrazino]-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide 
• 41371-06-6 N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-4-(5-ethyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylazo)-benzenesulfonamide 
• 41334-09-2 4-(5-ethyl-4,6-dioxo-2-thioxo-hexahydro-pyrimidin-5-ylazo)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide 
• 97665-54-8 (etazolato)2 nickel 

Relevant articles and documents

Discovery and characterization of carbamothioylacrylamides as EP2 selective antagonists

Prostanoid receptor EP2 is emerging as a novel target for development of anti-inflammatory drugs for the treatment of chronic neurodegenerative and peripheral diseases; however, the availability of EP2 antagonist probes for exploration of peripheral disease models is very limited. We now report identification and characterization of a novel chemical class of compounds that show nanomolar potency and competitive antagonism of the EP2 receptor. A compound in this class, TG6-129, showed prolonged plasma half-life and did not cross the blood-brain barrier. This compound also suppressed the induction of inflammatory mRNA markers in a macrophage cell line upon activation of EP2. Thus, this compound could be useful as a probe for a variety of peripheral chronic inflammatory diseases such as rheumatoid arthritis and chronic obstructive pulmonary disease, in which EP2 appears to play a pathogenic role.

SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME

Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.

p-NITROBENZENESULFONYL CHLORIDE AS A RAW MATERIAL FOR THE MANUFACTURE OF SULFANILAMIDE PREPARATIONS

-