N,N-diethyl-4-hydroxybenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4.6 g (0.0188 mole) of 4-chlorophenyl trifluoromethyl sulfone and 4.8 g (0.0210 mole) of N,N-diethyl-4-hydroxybenzenesulfonamide in 80 ml of DMSO was added 2.9 g (0.0210 mole) of K2CO3. The mixture was heated at 100° C. for 3.25 hrs and cooled. The mixture was poured into aqueous NaOH and the crystalline product collected by filtration, washed well with water and dried, which gave 7.25 g (88.2% yield) of product. Recrystallization from 2-propanol afforded purified N,N-diethyl-4-(4-((trifluoromethyl)sulfonyl)phenoxy)benzenesulfonamide, mp 83°-84° C. cooled the crystalline product collected by filtration washed well with water dried

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4.6 g (0.0188 mole) of 4-chlorophenyl trifluoromethyl sulfone and 4.8 g (0.0210 mole) of N,N-diethyl-4-hydroxybenzenesulfonamide in 80 ml of DMSO was added 2.9 g (0.0210 mole) of K2CO3. The mixture was heated at 100° C. for 3.25 hrs and cooled. The mixture was poured into aqueous NaOH and the crystalline product collected by filtration, washed well with water and dried, which gave 7.25 g (88.2% yield) of product. Recrystallization from 2-propanol afforded purified N,N-diethyl-4-(4-((trifluoromethyl)sulfonyl)phenoxy)benzenesulfonamide, mp 83°-84° C. cooled the crystalline product collected by filtration washed well with water dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6.73 g (0.0294 moles) of N,N-diethyl-4-hydroxybenzenesulfonamide in 150 ml of DMSO was added 1.18 g (0.0294 moles) of NaOH. The mixture was heated to 60° C. and 4.88 g (0.0267 moles) of 2-chloro-5-nitrobenzonitrile was added and the mixture heated at 75° C. for 3 hrs. The reaction mixture was cooled and poured into a solution of 400 ml of 2 N aqueous NaOH and 300 ml of water. The product was collected by filtration, washed well with water and dried to obtain 8.8 g of product (88% yield). Recrystallization from ethanol afforded purified N,N-diethyl-4-(2-cyano-4-nitrophenoxy)benzenesulfonamide, mp 163°-164° C. the mixture heated at 75° C. for 3 hrs The reaction mixture was cooled The product was collected by filtration washed well with water dried