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

HRID 13801

반응식

HRID 13801 반응식
[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

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychloride2회HCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f6e58b0c76784b2495f47166236c83c3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728141B2

연결된 노트

불러오는 중…