Benzenesulfonamide → HCID 21566305, compound

Participants

Reaction Steps

2.9 g of N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)- benzene-sulfonyl]-N'-(4.4-dimethylcyclohexyl)-thiourea (prepared by reaction of 4-[β-<2-methoxy-5-chlorobenzamido>-ethyl]-benzenesulfonamide with cyclohexyl mustard oil in dioxane/acetone in the presence of potassium carbonate) melting point 175°-177°C and decomposition, are dissolved in 250 ml acetone. An aqueous solution of 0.7 g sodium nitrite is added and while stirring is continued at 5°C, 15 ml of 5N acetic acid are added dropwise. After stirring for 21/2 hours acetone is distilled off. The residue is dissolved in dilute sodium hydroxide solution, the solution is clarified with charcoal and acidified. There is obtained a crystalline precipitate of N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N'-(4.4-dimethylcyclohexyl)-urea, which is filtered off with suction and recrystallized from dilute methanol. The substance melts at 174°-176°C. 2. (a) 5.38 g of N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)benzene-sulfonyl]-N'-(4.4-dimethylcyclohexyl)-thiourea are dissolved in 5 ml dioxane and 250 ml methanol. Then 2.16 g of mercury peroxide are added and stirring is continued for 4 hours at 60°C. The mercury sulfide formed is filtered off, and the filtrate is half concentrated and water is added. After abandoning during the night a crystalline precipitate has formed, which is filtered off with suction and recrystallized from dilute methanol. The N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N'-(4.4-dimethylcyclohexyl)-isoureamethylether thus obtained melts at 149°-151°C.

Provenance & Evidence