6-[(2-Fluorophenyl)methyl]-3(2H)-pyridazinone → 6-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one

HRID 1419498노트

반응식

HRID 1419498 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[F:5][C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[CH2:8][C:9]1[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=1.[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[C:22]=1[C:23](Cl)=[O:24].C(Cl)(=O)C(Cl)=O.C(Cl)Cl>C(Cl)Cl.CN(C=O)C>[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[C:22]=1[C:23]([C:17]1[CH:16]=[C:7]([C:6]([F:5])=[CH:19][CH:18]=1)[CH2:8][C:9]1[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=1)=[O:24]

참가 물질

7

반응물 4

HCID 14805366-[(2-Fluorophenyl)methyl]-3(2H)-pyridazinoneHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21906498HCID 21906498, 화합물

생성물 1

HCID 543549036-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

AlCl3 (1.75 g, 13.1 mmol) was added to a solution of 6-(2-fluorobenzyl)-2H-pyridazin-3-one (0.9 g, 4.4 mmol) [prepared as described above] in methylene chloride (20 ml) at ambient temperature and under a nitrogen atmosphere. 2,4,6-trichlorobenzoyl chloride [(1.98 g, 8.78 mmol) prepared from the corresponding acid by treatment with oxalyl chloride/ methylene chloride with a trace of DMF] was added to the slurry. After stirring overnight, the reaction was quenched with ice. The product was extracted into ethyl acetate, and dried over MgSO4. The solvent was removed in vacuo and the crude product was chromatographed on a silica gel column (ether) to give impure 6-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one (0.43 g). Recrystallization from acetone/hexanes mixture gave pure 6-[3-(2,4,6-trichlorobenzoyl)-6-fluorobenzyl)-2H-pyridazin-3-one (0.34 g, 18% yield) as a solid, mp 185.0°-185.3° C.

후처리

  1. additionwas added to the slurry
  2. customthe reaction was quenched with ice
  3. extractionThe product was extracted into ethyl acetate
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customthe crude product was chromatographed on a silica gel column (ether)

출처 및 근거

ORD 기록
ord-62604a8fcbce4deaa6012287b1433ede
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886178

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