Reaktion #8877

Reaktionsgleichung

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

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the slow addition
2. 2
   SonstigeMost of the DMF was then removed in vacuo before the reaction
3. 3
   workup.ADDITIONwas diluted with aqueous 18% citric acid solution
4. 4
   ExtraktionThe mixture was extracted twice with methylene chloride
5. 5
   Waschenthe organic layers were washed with a portion of brine
6. 6
   TrocknenThe combined organic layers were dried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe solid residue was triturated with ether
9. 9
   Filtrationfiltered
10. 10
    Sonstigeair dried
11. 11
    Sonstigeto afford the product

Vorschrift

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).

Quelle