Water → 3-(1-cyano-1-methylethyl)-N-{3-[(5-nitropyridin-2-yl)oxy]-4-(trifluoromethyl)phenyl}benzamide

HRID 1800499

反応式

HRID 1800499 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[C:24]([OH:32])[CH:23]=1)=[O:20])([CH3:15])[CH3:14])#[N:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[C:24]([O:32][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:23]=1)=[O:20])([CH3:15])[CH3:14])#[N:12]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 684185013-(1-cyano-1-methylethyl)-N-[3-hydroxy-4-(trifluoromethyl)phenyl]benzamide

生成物 1

HCID 684185283-(1-cyano-1-methylethyl)-N-{3-[(5-nitropyridin-2-yl)oxy]-4-(trifluoromethyl)phenyl}benzamide収率 66.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-chloro-5-nitropyridine (2.00 g, 5.74 mmol) and 3-(1-cyano-1-methylethyl)-N-[3-hydroxy-4-(trifluoromethyl)phenyl]benzamide (955 mg, 6.02 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (1.18 g, 8.61 mmol), and the mixture was stirred at 80° C. for 20 hr. After the reaction mixture was cooled to room temperature, water (150 mL) was added, and the mixture was twice extracted with ethyl acetate/hexane (75 mL/75 mL). The combined organic layer was washed with saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70). The obtained solution was concentrated under reduced pressure to give the title compound (1.79 g, 66%) as a yellow amorphous substance.

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe mixture was twice extracted with ethyl acetate/hexane (75 mL/75 mL)
  3. washThe combined organic layer was washed with saturated brine (150 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70)
  8. concentrationThe obtained solution was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-7ccec59d610d43e5ac12086bd27c1dfc
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

関連ノート

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