Cyanoacetamide → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 8805

反応式

HRID 8805 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[CH:10]N(C)C.[C:22]([CH2:24][C:25]([NH2:27])=[O:26])#[N:23].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:27][C:25](=[O:26])[C:24]([C:22]#[N:23])=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 686588401-(2-Chlorophenyl)-2-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

生成物 1

HCID 219849076-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
95 °C

実験手順

A solution of the crude product from step A dissolved in 80 mL of DMF containing 4.4 mL methanol and 4.61 g cyanoacetamide was transferred by cannula into a flask containing a suspension of NaH (4.98 g, 60% dispersion in mineral oil, freed of excess oil by washing with hexane just prior to use) in DMF (40 mL). The solution was heated to 95° C. for 2.5 hours then concentrated. The residue was dissolved in ethyl acetate, washed twice with 10% aqueous NaHSO4, and twice with water before concentrating to a solid. The solid was suspended in warm ethanol and then cooled, and the title compound was subsequently isolated by filtration and dried in vacuo.

後処理

  1. additioncontaining
  2. washby washing with hexane just
  3. concentrationthen concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed twice with 10% aqueous NaHSO4
  6. concentrationtwice with water before concentrating to a solid
  7. temperaturecooled

出典と根拠

ORDレコード
ord-a4bf6cda5e1b41fbb814ac2110f72af8
出典データセット
uspto-grants-2006_08
特許番号
US07091216B2

関連ノート

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