Name | 2-(2-chloroethoxy)benzene sulfonamide |
Synonyms | Triasulfuron metabolite 2-(2-Chlorethoxy)benzolsulfonamid 2-(2-Chloroethoxy)benzenesulfonamide 2-(2-chloroethoxy)benzene sulfonamide 2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE |
CAS | 82097-01-6 |
InChI | InChI=1/C8H10ClNO3S/c9-5-6-13-7-3-1-2-4-8(7)14(10,11)12/h1-4H,5-6H2,(H2,10,11,12) |
Molecular Formula | C8H10ClNO3S |
Molar Mass | 235.69 |
Density | 1.384g/cm3 |
Melting Point | 119 °C |
Boling Point | 421.1°C at 760 mmHg |
Flash Point | 208.5°C |
Vapor Presure | 2.68E-07mmHg at 25°C |
Appearance | Form Solid, color White to Off-White |
pKa | 9.97±0.60(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.559 |
Physical and Chemical Properties | Chemical quality is a white solid, m.p.118 ~ 119 ℃, insoluble in water, soluble in benzene, toluene, chlorobenzene and other organic solvents. |
Use | Intermediates for the synthesis of sulfonylurea pesticides |
solubility | DMSO (Slightly), Methanol (Slightly) |
The preparation method is to add 4-chlorophenol and dichloroethane, catalyst and sodium hydroxide solution in the reaction kettle, heat and stir, and react for several hours to obtain 1-(4-chlorophenoxy)-2-Chloroethane, the compound is sulfonated by chlorosulfonic acid dropwise at 0~5 ℃ in dichloroethane, the reaction temperature is 25~30 ℃, and the temperature is kept for 3, 2-(β-chloroethoxy)-5-chlorobenzenesulfonyl chloride was obtained. The compound is slowly added with 30% sodium hydroxide solution at 35~40 ℃, and the obtained sodium 5-chloro-2-(β-chloroethoxy) benzene sulfonate is catalyzed at 40~60 ℃ with palladium/carbon as catalyst and pressure 100 kPa for hydrogenation, chlorine atoms on benzene ring are removed, and 30% sodium hydroxide solution is continuously added to maintain the pH value at 9.5~11.5 to obtain sodium 2-(β-chloroethoxy) benzene sulfonate, dilute with chlorobenzene, add catalyst DMF, and continuously introduce phosgene to maintain it at 90 ℃ for 2~3 h to obtain 2-(β-chloroethoxy) benzenesulfonyl chloride. Add a water layer, separate the organic layer and react with 30% ammonia solution to generate 2-(β-chloroethoxy) benzenesulfonamide chlorobenzene solution, and heat to remove chlorobenzene to obtain the finished.
It is also possible to use divinyl carbonate instead of 1, 2-dichloroethane for the reaction.
In addition, 2-(β-chloroethoxy)-aniline can also be used as raw material through diazotization, sodium bisulfite and catalyst copper sulfate and hydrochloric acid to generate 2-(β-chloroethoxy) benzenesulfonyl chloride, and then react with ammonia to form a finished product.