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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
ノート
印刷プレビュー

反応式

HRID 424847 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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
収率 97%

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-56d5636957a0466dba4866b95eba94c6
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08106077B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート