Phase-Transfer-CatalysedN-Alkylation of Carboxamides and Sulfonamides

Stary Rypin – od grodu do miasta

“…Jedynie materiał źródłowy był przedmiotem pracy magisterskiej Anny Łytki (2007). W 1980 roku badania powierzchniowe na terenie obiektu obronnego przeprowadził Andrzej Gajda (1981; por. też Kajzer, Horonziak 1995, s. 199-200).…”

Formation of 6-chloro-4-phenyl-2-quinolone in reaction of dimethyl sulfate with 2-(acetylamino)-5-chlorobenzophenone under phase-transfer conditions

“…At the same time, these compounds can be prepared from 2-(acetylamino)-5-chlorobenzophenone (III) [2] and 2-(N-acetyl-N-methylamino)-5-chlorobenzophenone (IV). To prepare compound IV, alkylation of ketone III with dimethyl sulfate under phase-transfer conditions at elevated temperatures was tried [3].…”

“…Under the conditions described in [3], i.e. by refluxing compound III [2] and dimethyl sulfate in toluene ÄÄÄÄÄÄÄÄÄÄÄÄ containing a mixture of NaOH and K 2 CO 3 , as well as tetrabutylammonium hydrosulfate as catalyst, no compound IV was formed.…”

“…Ketone IV is prepared in quantitative yield by the procedure in [3] but at 18320oC. Treatment of compound IV with a mixture of ethanol and 20% H 2 SO 4 (1 : 2, v/v) provides 5-chloro-2-(methylamino)benzophenone (V) in 98% yield [2].…”

“…Thus, the reaction of benzophenone I with dimethyl sulfate, performed as described in [3], involves both N-methylation and cyclization and gives a mixture of 2-quinolones. Lowering the reaction temperature to 18320oC allows substituted benzophenone IV to be prepared in quantitative yield.…”