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

HRID 70254

반응식

HRID 70254 반응식
[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]

참가 물질

7

반응물 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 6098995-Bromo-2-chlorotolueneHCID 178478050HCID 178478050, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-eb7316c064804edc9d13bdbb0e2da187
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822521B2

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