반응 #8877

반응 방정식

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

용매

DMF

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the slow addition
2. 2
   기타Most of the DMF was then removed in vacuo before the reaction
3. 3
   workup.ADDITIONwas diluted with aqueous 18% citric acid solution
4. 4
   추출The mixture was extracted twice with methylene chloride
5. 5
   세척the organic layers were washed with a portion of brine
6. 6
   건조The combined organic layers were dried over anhydrous sodium sulfate
7. 7
   농축concentrated in vacuo
8. 8
   기타The solid residue was triturated with ether
9. 9
   여과filtered
10. 10
    기타air dried
11. 11
    기타to afford the product

실험 절차

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).

출처