تفاعل #8877

معادلة التفاعل

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

المذيبات

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the slow addition
2. 2
   أخرىMost of the DMF was then removed in vacuo before the reaction
3. 3
   workup.ADDITIONwas diluted with aqueous 18% citric acid solution
4. 4
   استخلاصThe mixture was extracted twice with methylene chloride
5. 5
   غسيلthe organic layers were washed with a portion of brine
6. 6
   تجفيفThe combined organic layers were dried over anhydrous sodium sulfate
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe solid residue was triturated with ether
9. 9
   ترشيحfiltered
10. 10
    أخرىair dried
11. 11
    أخرىto afford the product

الإجراء التجريبي

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).

المصدر