2-(Phenylmethanesulfinyl)aniline → HCID 13672816, compound

Reaction equation

[CH2:1]([S:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1N)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+]>OS(O)(=O)=O.O>[CH:14]1[C:15]2[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:1][S:8](=[O:9])[C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

Procedure

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: