A Brønsted Organic Acid Forming Solid State Salts with Chemically Stable Cationic Species
Diazotization of aniline: A solution of
o-benzensulfoimide (2.63 g, 12 mmol) in glacial AcOH (40 mL) is slowly added, over a period of 10 min, to a stirred solution of aniline (0.93 g, 10 mmol) in the same solvent (20 mL), previously cooled to 0-5 ℃ in an ice bath.
i-Pentyl nitrite (1.28 g, 11 mmol) is added dropwise at such a rate that the temperature did not exceed 5 ℃ (about 10 min). After the addition is completed, the cooling bath is removed and the mixture is maintained under stirring for a further 5 min. Then anhyd. Et
2O is added to complete the precipitation of the diazonium salt that is gathered by filtration on a Buchner funnel and washed several times on the funnel with anhyd. Et
2O (6 x 6 mL) to complete the elimination of AcOH. After drying under reduced pressure, the dry title compound is obtained in 98% yield (3.18 g).