Phosphorus oxychloride → 2-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile

HRID 13801

反応式

HRID 13801 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=O)[C:12]([C:16]#[N:17])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.O=P(Cl)(Cl)[Cl:27]>>[Cl:27][C:13]1[C:12]([C:16]#[N:17])=[CH:11][C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:14]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychloride2 回HCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

生成物 1

HCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile

反応条件

温度
100 °C

実験手順

To 6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-nitrile (40.75g) was added POCl3 (20 mL). The reaction was heated to 100° C. for 13 hours. After cooling to room temperature the excess POCl3 was removed in vacuo before the residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 solution. The solution was concentrated and purified via flash chromatography on silica gel with a gradient elution of 30% to 100% CH2Cl2 in hexane affording the title compound. HPLC/MS: 392.9 (M+1), 394.9 (M+3); Rt=4.45 min.

後処理

  1. customwas removed in vacuo before the residue
  2. dissolutionwas dissolved in CH2Cl2
  3. washwashed with saturated aqueous NaHCO3 solution
  4. concentrationThe solution was concentrated
  5. custompurified via flash chromatography on silica gel with a gradient elution of 30% to 100% CH2Cl2 in hexane affording the title compound

出典と根拠

ORDレコード
ord-f6e58b0c76784b2495f47166236c83c3
出典データセット
uspto-grants-2010_06
特許番号
US07728141B2

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