Sodium Bicarbonate → N-(4-cyano-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide

HRID 1800488ノート

反応式

HRID 1800488 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1.C(=O)([O-])O.[Na+].[C:16]([C:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])([CH3:20])[CH3:19])#[N:17]>O1CCCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([C:18]([C:16]#[N:17])([CH3:19])[CH3:20])[CH:22]=2)=[CH:3][C:4]=1[OH:10])#[N:7]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 124686824-Amino-2-hydroxybenzonitrileHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

生成物 1

HCID 68416945N-(4-cyano-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide収率 44%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a two-layer solution of 4-amino-2-hydroxybenzonitrile (3.16 g, 23.5 mmol) in tetrahydrofuran (80 mL)/1N aqueous sodium hydrogen carbonate solution (80 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 18 hr. The aqueous layer was separated, and extracted with ethyl acetate (100 mL). The combined organic layer was washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 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 dissolved in methanol (300 mL), anhydrous potassium carbonate (3.5 g) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate (300 mL) was added to the obtained residue, and the mixture was washed with water (150 mL) and 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 recrystallized from ethyl acetate (50 mL)/hexane (50 mL) to give the title compound (3.10 g, 44%) as a pale-brown powder.

後処理

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe combined organic layer was washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 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. dissolutionThe obtained residue was dissolved in methanol (300 mL)
  8. additionanhydrous potassium carbonate (3.5 g) was added
  9. stirringthe mixture was stirred at room temperature for 2 hr
  10. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (300 mL)
  11. additionwas added to the obtained residue
  12. washthe mixture was washed with water (150 mL) and saturated brine (150 mL)
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationThe insoluble material was filtered off
  15. concentrationthe filtrate was concentrated under reduced pressure
  16. customThe obtained residue was recrystallized from ethyl acetate (50 mL)/hexane (50 mL)

出典と根拠

ORDレコード
ord-a85371b3566a419b8ebed9cbbac12e91
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

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