2-(Phenylmethanesulfinyl)aniline → HCID 13672816, compound

Participants

Reaction Steps

To a stirred suspension of benzyl-(2-aminophenyl)-sulfoxide (1.9 g; 0.008 mol) in 30 ml of 11% H2SO4 was added a solution of sodium nitrite (0.78 g; 0.011 mol) in 20 ml of water at about 0° C. After 1 hour at 0° C. to the yellow solution was quickly added a solution of cupric nitrate trihydrate (34.2 g; 0.140 mol) in 75 ml of water and cuprous oxide (1.33 g; 0.009 mol). The solution was allowed to warm to room temperature and stirred for further 5 hours. The solid was filtered and treated with hot ethyl acetate. The solution was dried over sodium sulfate concentrated and the residue was crystallized from ethyl acetate/pentane (1:4) to give 6H-dibenzo[b,d]thiopyran-5-oxide (1.25 g; yield 71%); m.p. 97°-100° C. By proceeding analogously the following compounds were obtained:

Provenance & Evidence