Salicylaldehyde oxime → 1-(3-methyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole

HRID 70254

反応式

HRID 70254 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=NO)C1C(=CC=CC=1)O.Br[C:24]1[CH:25]=[CH:26][C:27]([Cl:31])=[C:28]([CH3:30])[CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu]=O>[CH3:30][C:28]1[CH:29]=[C:24]([N:10]2[CH:11]=[CH:12][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:9]2)[CH:25]=[CH:26][C:27]=1[Cl:31]

参加物

7

反応物 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 6098995-Bromo-2-chlorotolueneHCID 178478050HCID 178478050、化合物

生成物 1

HCID 667871901-(3-methyl-4-chlorophenyl)-3-(3-chlorophenyl)-1H-pyrazole収率 21.7%

試薬・触媒・溶媒 2

HCID 14829Copper oxide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

A mixture of 3-(3-chlorophenyl)-1H-pyrazole (5.3 g, 29.8 mmol) (prepared according to the method given in European Patent Publication EP 538156), salicylaldoxime (0.58 g, 4.25 mmol), 5-bromo-2-chlorotoluene (2.8 g, 21.3 mmol), copper oxide (0.15 g, 1.06 mmol) and cesium carbonate (11.8 g, 36.2 mmol) in 20 mL of N,N-dimethylformamide was heated at 140° C. overnight and then allowed to cool to room temperature. The resulting suspension was filtered and the filtrate was concentrated under reduce pressure. The resulting residue was purified by medium pressure liquid chromatography (2 to 10% gradient of ethyl acetate in hexanes as eluant) to give the title compound as a white solid (1.4 g).

後処理

  1. customprepared
  2. temperatureto cool to room temperature
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified by medium pressure liquid chromatography (2 to 10% gradient of ethyl acetate in hexanes as eluant)

出典と根拠

ORDレコード
ord-eb7316c064804edc9d13bdbb0e2da187
出典データセット
uspto-grants-2014_09
特許番号
US08822521B2

関連ノート

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