반응 #1933442

반응 방정식

2-amino-N-(4-sec-butylphenyl)benzamide

4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde

sodium hydrogen sulphite

p-toluenesulfonic acid

→

title compound ( E )

3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

용매

N,N-dimethyl acetamide

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   기타The solvent was removed under reduced pressure and water (100 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   추출The mixture was extracted with ethyl acetate (200 mL)
5. 5
   세척The organic phase was washed with water (2×100 mL)
6. 6
   건조brine (100 mL), and dried over anhydrous Na2SO4
7. 7
   기타Removal of solvent
8. 8
   기타gave crude compound, which
9. 9
   기타was purified by the Simpliflash system (30% ethyl acetate in hexanes as eluent)

실험 절차

To a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (1.27 g, 4.73 mmol) in N,N-dimethyl acetamide (20 mL) were added 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (D) (0.92 g, 4.7 mmol), sodium hydrogen sulphite (58.5 wt %) (0.95 g, 5.2 mmol) and p-toluenesulfonic acid (0.18 g, 0.95 mmol). The reaction mixture was stirred at 120° C. overnight, and cooled to room temperature. The solvent was removed under reduced pressure and water (100 mL) was added. The mixture was extracted with ethyl acetate (200 mL). The organic phase was washed with water (2×100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. Removal of solvent gave crude compound, which was purified by the Simpliflash system (30% ethyl acetate in hexanes as eluent) to give the title compound (E) as a white solid. Yield: 0.34 g (16%). MP 152-153° C. 1H-NMR (400 MHz, CDCl3): δ 8.36-8.34 (m, 1H), 7.81-7.80 (m, 2H), 7.54-7.50 (m, 1H), 7.13 (d, J=6.26 Hz, 2H), 7.06 (d, J=8.21 Hz, 2H), 6.98 (s, 2H), 3.92-3.88 (m, 2H), 3.78-3.76 (m, 2H), 2.56-2.54 (m, 1H), 2.13 (s, 6H), 2.06 (t, J=6.26 Hz, 1H), 1.60-1.48 (m, 2H), 1.20 (d, J=7.04 Hz, 3H), 0.727 (t, J=7.43 Hz, 3H). MS (ES+) m/z: 443.01 (M+1) (100%).

출처