2-benzylsulfanylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196°-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1H), 8.36 (dd, J=8.1, 0.8 Hz, 1H), 7.50-7.62 (m, 2H), 7.28-7.45 (m, 4H), 7.16-7.26 (m, 4H), 7.00-7.08 (m, 2H), 6.24 (d, J=1.8 Hz, 1H), 3.97 (s, 2H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34. the mixture was heated to reflux under a Dean-Stark trap the reaction was concentrated the residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196°-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1H), 8.36 (dd, J=8.1, 0.8 Hz, 1H), 7.50-7.62 (m, 2H), 7.28-7.45 (m, 4H), 7.16-7.26 (m, 4H), 7.00-7.08 (m, 2H), 6.24 (d, J=1.8 Hz, 1H), 3.97 (s, 2H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34. the mixture was heated to reflux under a Dean-Stark trap the reaction was concentrated the residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 mmoles of 2-benzylmercaptobenzaldehyde, 15 mmoles of nitroacetone and 10 mmoles of 3-aminocrotonic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-phenyl]-amide in 30 ml of isopropanol are heated at 60°-70° C. for 10 hours. The reaction mixture is concentrated and the residue is taken up in chloroform and chromatographed over silica gel using chloroform to which methanol is added. The product is recrystallized from isopropanol. The reaction mixture is concentrated chromatographed over silica gel is added The product is recrystallized from isopropanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 mmoles of 2-benzylmercaptobenzaldehyde, 15 mmoles of nitroacetone and 10 mmoles of 3-aminocrotonic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-phenyl]-amide in 30 ml of isopropanol are heated at 60°-70° C. for 10 hours. The reaction mixture is concentrated and the residue is taken up in chloroform and chromatographed over silica gel using chloroform to which methanol is added. The product is recrystallized from isopropanol. The reaction mixture is concentrated chromatographed over silica gel is added The product is recrystallized from isopropanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mmole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1 H), 8.36 (dd, J=8.1, 0.8 Hz, 1 H), 7.50-7.62 (m, 2 H), 7.28-7.45 (m, 4 H), 7.16-7.26 (m, 4 H), 7.00-7.08 (m, 2 H), 6.24 (d, J=1.8 Hz, 1 H), 3.97 (s, 2 H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34. the mixture was heated to reflux under a Dean-Stark trap the reaction was concentrated the residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mmole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1 H), 8.36 (dd, J=8.1, 0.8 Hz, 1 H), 7.50-7.62 (m, 2 H), 7.28-7.45 (m, 4 H), 7.16-7.26 (m, 4 H), 7.00-7.08 (m, 2 H), 6.24 (d, J=1.8 Hz, 1 H), 3.97 (s, 2 H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34. the mixture was heated to reflux under a Dean-Stark trap the reaction was concentrated the residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196°-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1H), 8.36 (dd, J=8.1, 0.8 Hz, 1H), 7.50-7.62 (m, 2H), 7.28-7.45 (m, 4H), 7.16-7.26 (m, 4H), 7.00-7.08 (m, 2H), 6.24 (d, J=1.8 Hz, 1H), 3.97 (s, 2H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34. the mixture was heated to reflux under a Dean-Stark trap the reaction was concentrated the residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 mmoles of 2-benzylmercaptobenzaldehyde, 15 mmoles of nitroacetone and 10 mmoles of 3-aminocrotonic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-phenyl]-amide in 30 ml of isopropanol are heated at 60°-70° C. for 10 hours. The reaction mixture is concentrated and the residue is taken up in chloroform and chromatographed over silica gel using chloroform to which methanol is added. The product is recrystallized from isopropanol. The reaction mixture is concentrated chromatographed over silica gel is added The product is recrystallized from isopropanol

Conditions: temp:22.01; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mmole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1 H), 8.36 (dd, J=8.1, 0.8 Hz, 1 H), 7.50-7.62 (m, 2 H), 7.28-7.45 (m, 4 H), 7.16-7.26 (m, 4 H), 7.00-7.08 (m, 2 H), 6.24 (d, J=1.8 Hz, 1 H), 3.97 (s, 2 H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34. the mixture was heated to reflux under a Dean-Stark trap the reaction was concentrated the residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-[(Phenylmethyl)thio]benzaldehyde (2.28 g, 10 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (1.97 g, 10 mmole, 1 equiv.), and piperidine (0.5 ml, 5 mole, 0.5 equiv.) were combined in toluene (50 ml), and the mixture was heated to reflux under a Dean-Stark trap. After 3 hr, the reaction was concentrated and the residue was chromatographed on silica gel (50% EtOAc/CHCl3) to afford 2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.90 g, 55%) as a brownish-yellow foam. Recrystallization from CHCl3 /EtOAc gave light yellow crystals (1.39 g): mp 196°-197° C.; TLC (50% EtOAc/CHCl3) Rf 0.31; 1H NMR (CDCl3) δ8.63 (br s, 1H), 8.36 (dd, J=8.1, 0.8 Hz, 1H), 7.50-7.62 (m, 2H), 7.28-7.45 (m, 4H), 7.16-7.26 (m, 4H), 7.00-7.08 (m, 2H), 6.24 (d, J=1.8 Hz, 1H), 3.97 (s, 2H); IR (KBr) 2100-3200 (br), 1632, 1594, 1530, 1497, 1439 cm-1 ; MS (NH3), m/e (%) 344.1 (100, (M+H)+), 254.2 (26.9). Anal. Calcd for C22H17NOS: C, 76.54; H, 4.87; N, 3.91; S, 9.12. Found: C, 76.94; H, 4.99; N, 4.08; S, 9.34. the mixture was heated to reflux under a Dean-Stark trap the reaction was concentrated the residue was chromatographed on silica gel (50% EtOAc/CHCl3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 mmoles of 2-benzylmercaptobenzaldehyde, 15 mmoles of nitroacetone and 10 mmoles of 3-aminocrotonic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-phenyl]-amide in 30 ml of isopropanol are heated at 60°-70° C. for 10 hours. The reaction mixture is concentrated and the residue is taken up in chloroform and chromatographed over silica gel using chloroform to which methanol is added. The product is recrystallized from isopropanol. The reaction mixture is concentrated chromatographed over silica gel is added The product is recrystallized from isopropanol