Reaktion #816456

Reaktionsgleichung

4-chloro-2-ethyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide

4-morpholinoaniline

→

title compound

Ausbeute 29.0%

2-Ethyl-4-[(4-morpholin-4-ylphenyl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Ausbeute 29.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was purified by preparative HPLC (C8 50×250, 0.1M NH4OAc/MeCN, gradient) which
2. 2
   Sonstigegave impure product
3. 3
   SonstigeRepurification

Vorschrift

A solution of 4-chloro-2-ethyl-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.217 g, 0.80 mmol) and 4-morpholinoaniline (0.285 g, 1.60 mmol) in DMF (2.0 mL) was heated at 110° C. for 15 mins in a microwave reactor. The mixture was purified by preparative HPLC (C8 50×250, 0.1M NH4OAc/MeCN, gradient) which gave impure product. Repurification was done by preparative HPLC (C8 50×250, 0.1M NMR OAc/MeCN, 50% MeCN isocratic) to give the title compound (0.096 g, 29%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.22-7.16 (m 1H), 7.12-7.09 (m, 4H), 6.62-6.57 (m 2H), 6.52-6.48 (m, 2H), 3.84 (q, 2H), 3.81-3.78 (m, 4H), 2.99-2.95 (m, 4H), 1.47 (t 3H); 13C NMR (500 MHz, CDCl3): δ 159.4, 149.2, 131.5, 129.5, 128.9, 128.4, 128.1, 125.1, 123.6, 115.6, 109.8, 66.9, 49.7, 35.6, 14.0; Mass Spectrum: M−H+ 414.

Quelle