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Acetonitrile → 4-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester

HRID 424847
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HRID 424847 반응식
BrC[C:3]1[N:7]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])[N:6]=[N:5][C:4]=1[C:16]([F:19])([F:18])[F:17].O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:32]([CH3:40])[CH:31]=2)=[C:23](C)[CH:22]=1.[C:42](=[O:45])([O-])[O-].[K+].[K+].[C:48](#N)C>>[CH3:37][O:36][C:34](=[O:35])[C:33]1[CH:38]=[CH:39][C:30]([CH2:29][N:28]([C:27]2[CH:22]=[CH:21][C:26]([O:45][CH2:42][C:3]3[N:7]([C:8]4[C:9]([Cl:15])=[CH:10][CH:11]=[CH:12][C:13]=4[Cl:14])[N:6]=[N:5][C:4]=3[C:16]([F:18])([F:17])[F:19])=[CH:25][C:24]=2[CH3:23])[CH3:48])=[CH:31][C:32]=1[CH3:40]
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참가 물질

5

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 667042144-{[(4-Hydroxy-2-methylphenyl)methylamino]methyl}-2-methyl benzoic acid, methyl esterHCID 866292535-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole

생성물 1

HCID 667042114-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester
수율 97%

반응 조건

온도
90 °C

실험 절차

To a solution of 5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole (15.65 g, 41.7 mmol) and 4-{[(4-hydroxy-2-methylphenyl)methylamino]methyl}-2-methyl benzoic acid, methyl ester (12.49 g, 41.7 mmol) in acetonitrile (120 mL) is added potassium carbonate (11.54 g, 83.4 mmol) at room temperature. The mixture is heated at 90° C. overnight. After 16 h, the reaction is cooled to room temperature and filtered through a pad of diatomaceous earth. The solvent is removed under reduced pressure. The residue is diluted with MTBE and washed with 2N NaOH, water, and brine. The organic layer is dried over magnesium sulfate, filtered, and evaporated to afford 4-[({4-[3-(2,6-dichlorophenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methylphenyl}-methylamino)-methyl]-2-methyl-benzoic acid methyl ester (24.2 g, 97%). ES/MS m/e 593 (M+1).

후처리

  1. temperaturethe reaction is cooled to room temperature
  2. filtrationfiltered through a pad of diatomaceous earth
  3. customThe solvent is removed under reduced pressure
  4. additionThe residue is diluted with MTBE
  5. washwashed with 2N NaOH, water, and brine
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-56d5636957a0466dba4866b95eba94c6
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106077B2

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