反応 #8877

反応方程式

3-dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one

cyanoacetamide

methanol

sodium hydride

→

6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-nitrile

溶媒

DMF

DMF

反応条件

後処理

1. 1
   workup.ADDITIONAfter the slow addition
2. 2
   その他Most of the DMF was then removed in vacuo before the reaction
3. 3
   workup.ADDITIONwas diluted with aqueous 18% citric acid solution
4. 4
   抽出The mixture was extracted twice with methylene chloride
5. 5
   洗浄the organic layers were washed with a portion of brine
6. 6
   乾燥The combined organic layers were dried over anhydrous sodium sulfate
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The solid residue was triturated with ether
9. 9
   ろ過filtered
10. 10
    その他air dried
11. 11
    その他to afford the product

実験手順

A solution of 3-dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one (14.4 mmol assumed) from Step A, cyanoacetamide (1.33 g, 15.8 mmol), and methanol (1.3 mL, 32 mmol) in DMF (35 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil) (1.45 g, 36 mmol) in DMF (16 mL) at rt. After the slow addition was complete, the reaction was heated to 95° C. for 2.5 h. Most of the DMF was then removed in vacuo before the reaction was diluted with aqueous 18% citric acid solution. The mixture was extracted twice with methylene chloride and the organic layers were washed with a portion of brine. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The solid residue was triturated with ether, filtered, and air dried to afford the product. HPLC/MS: 375 (M+1), 377 (M+3); Rt=3.47 min; 1H NMR (CDCl3): δ 6.96 (br d, J=8.4 Hz,2H), 7.14 (d, J=8.2 Hz, 1H), 7.25 (br d, J=8.4 Hz, 2H), 7.31 (dd, J=1.9 and 8.2 Hz, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.996 (s, 1H).

出典