3-Amino-p-cresol → 3-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamide

HRID 1800449

Reaktionsgleichung

Reaktionsgleichung von HRID 1800449
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])O.[Na+].[C:15]([C:17]1([C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=2)[C:23](Cl)=[O:24])[CH2:19][CH2:18]1)#[N:16]>O1CCCC1>[C:15]([C:17]1([C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=2)[C:23]([NH:1][C:2]2[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=2[CH3:8])=[O:24])[CH2:18][CH2:19]1)#[N:16]

Komponenten

5

Edukt 3

HCID 178203-Amino-p-cresolHCID 516892Sodium Bicarbonate2×HCID 866319823-(1-Cyanocyclopropyl)benzoyl chloride

Produkt 1

HCID 673125693-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a two-layer solution of 3-amino-4-methylphenol (5.92 g, 48.0 mmol) in tetrahydrofuran (40 mL )/1N aqueous sodium hydrogen carbonate solution (54 mL) was added a solution of 3-(1-cyanocyclopropyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 2 hr. Since the pH of the reaction mixture was 4-5, sodium hydrogen carbonate (900 mg, 10.7 mmol) was added to the mixture to adjust the pH to 8-9, and the reaction mixture was further stirred at room temperature for 1 hr. The aqueous layer was separated, and extracted with ethyl acetate (150 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. Ethyl acetate (25 mL)/hexane (50 mL) was added to the obtained suspension, and the mixture was stirred at room temperature for 20 min. The precipitate was collected by filtration, washed repeatedly with diisopropyl ether/hexane (1:1), and air-dried to give the title compound (12.2 g, 87%) as a pale-yellow powder.

Aufarbeitung

  1. additionwas added to the mixture
  2. stirringthe reaction mixture was further stirred at room temperature for 1 hr
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (150 mL)
  5. washThe combined organic layer was washed with saturated brine (150 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionEthyl acetate (25 mL)/hexane (50 mL) was added to the obtained suspension
  10. stirringthe mixture was stirred at room temperature for 20 min
  11. filtrationThe precipitate was collected by filtration
  12. washwashed repeatedly with diisopropyl ether/hexane (1:1)
  13. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-82810ef95c54460592ff9c29b44ec466
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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