141776-47-8

Basic information

• Product Name: 2-Ethylsulfonylimidazo[1,2-a]pyridine-3-sulfonamide
• Synonyms: 2-Ethylsulfonylimidazo[1,2-a]pyridine-3-sulfonamide;2-Ethylsulfonylimidazo[1,2-a]Pyridin-3-yl Sulfonamide;2-(Ethylsulphonyl)imidazo[1,2-a]pyridine-3-sulphonamide;2-(ethanesulfonyl)iMidazo[1,2-a]pyridine-3-sulfonaMide;2-(ETHYLSULFONYL)H-IMIDAZO[1,2-A] PYRIDINE-3-SULFONAMIDE;2-Ethyl Sulfonylimidazo(1,2-A) Pyridine-3-Sulfonaide;2-(ethanesulfonyl)iMidazo[1,2-a]pyrid
• CAS NO: 141776-47-8
• Molecular Formula: C₉H₁₁N₃O₄S₂
• Molecular Weight: 289.33
• EINECS: 207-196-9
• Product Categories: Pyridines derivates;Heterocycle-Pyridine series
• Mol File: 141776-47-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.67 g/cm³
• Refractive Index: 1.706
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.40±0.60(Predicted)
• CAS DataBase Reference: 2-Ethylsulfonylimidazo[1,2-a]pyridine-3-sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylsulfonylimidazo[1,2-a]pyridine-3-sulfonamide(141776-47-8)
• EPA Substance Registry System: 2-Ethylsulfonylimidazo[1,2-a]pyridine-3-sulfonamide(141776-47-8)

Safety Data

• Hazard Codes: Xi
• Statements: Xi:刺激性物质
• Hazardous Substances Data: 141776-47-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11N3O4S2/c1-2-17(13,14)8-9(18(10,15)16)12-6-4-3-5-7(12)11-8/h3-6H,2H2,1H3,(H2,10,15,16)

Synthetic route

2-ethylthioimidazo[1,2-a]pyridine-3-sulfonamide → 2-ethylsulfonylimidazo[1,2a]pyridine-3-sulfonamide (141776-47-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In N-methyl-acetamide; water

O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate (89392-03-0) + 2-ethylsulfonylimidazo[1,2a]pyridine-3-sulfonamide (141776-47-8) → N-(2-Ethylsulfonylimidazo[1,2-a]pyridin-3-ylsulfonyl)-N-(4,6-dimethoxy-2-pyrimidinyl)urea

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile	91.3%

5-chloro-2,3-difluoropyridine (89402-43-7) + (R)-2-(4-hydroxyphenoxy)propionic acid (94050-90-5) + 2-ethylsulfonylimidazo[1,2a]pyridine-3-sulfonamide (141776-47-8) → (R)-2-ethanesulfonylimidazo[1,2-a]pyridine-3-sulfonic acid [2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl]amide (1361405-60-8)

Conditions	Yield
Stage #1: 5-chloro-2,3-difluoropyridine; (R)-2-(4-hydroxyphenoxy)propionic acid With potassium phosphate; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 50 - 60℃; for 2h; Stage #2: With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 5 - 25℃; for 1.16667h; Stage #3: 2-ethylsulfonylimidazo[1,2a]pyridine-3-sulfonamide In N,N-dimethyl-formamide	74%

2-pyrrolidinon (616-45-5) + 2-ethylsulfonylimidazo[1,2a]pyridine-3-sulfonamide (141776-47-8) → 2-(ethylsulfonyl)-N-(pyrrolidin-2-ylidene)imidazo[1,2-a]pyridine-3-sulfonamide

Conditions	Yield
With diazoacetic acid ethyl ester; manganese(II) perchlorate hexahydrate In cyclohexane at 90℃; for 12h; chemoselective reaction;	58%

phenyl chloroformate (1885-14-9) + 2-ethylsulfonylimidazo[1,2a]pyridine-3-sulfonamide (141776-47-8) → C16H15N3O6S2 (905926-26-3)

Conditions	Yield
With triethylamine In acetonitrile at 3 - 20℃;

Downstream Products

• 1361405-60-8 (R)-2-ethanesulfonylimidazo[1,2-a]pyridine-3-sulfonic acid [2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl]amide 
• 905926-26-3 C₁₆H₁₅N₃O₆S₂ 

Relevant articles and documents

Herbicidal imidazo[1,2-a]pyridin-3-ylsulfonylurea

A herbicide comprising the sulfonylurea derivatives of the formula (I): STR1 wherein Q is --CH=CH-- or --S--, R is C1-3 alkyl, and X is --OCH3 or --CH3 ; or a salt thereof, are useful for the control of undesired vegetation, for example, black glass (Alopecurus myosuroides) or downy brome (Bromus tectorum L.) in the presence of many valuable small grain cereals such as wheat, barley, oats and rye. The herbicide is also unexpectedly tolerant to small grain cereals such as wheat, barley, oats and rye.