Reaktion #414877

Reaktionsgleichung

chlorosulfonyl isocyanate

m-acetamidophenol

sulfamoyl chloride

→

desired product

N-[3-[(Aminosulfonyl)oxy]phenyl]acetamide

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe product was isolated by chromatography on 100 g silica gel
2. 2
   Wascheneluted first with 7:3 methylene chloride/acetonitrile
3. 3
   Temperaturincreasing the proportion of acetonitrile in the eluting solvent
4. 4
   SonstigeThe main fraction was evaporated
5. 5
   Sonstigetriturated with isopropyl alcohol/isopropyl ether

Vorschrift

By the same method described for Example 62, the title compound was prepared from m-acetamidophenol (12.10 g, 0.08 m), reacting with the sulfamoyl chloride generated from water and chlorosulfonyl isocyanate. The crude product contained desired product and starting material. The product was isolated by chromatography on 100 g silica gel, eluted first with 7:3 methylene chloride/acetonitrile and then increasing the proportion of acetonitrile in the eluting solvent. The main fraction was evaporated and triturated with isopropyl alcohol/isopropyl ether to give 4 g of white solid, recrystallized from acetonitrile/isopropyl ether, and dried in vacuum at 60° C. overnight to give 3.73 g of solid, mp 148°-149° C.

Quelle