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

HRID 2190367

Reaktionsgleichung

Reaktionsgleichung von HRID 2190367
[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 hydrogencarbonate 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 reaction mixture showed pH 4-5, sodium hydrogencarbonate (900 mg, 10.7 mmol) was added 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. To the obtained suspension was added ethyl acetate (25 mL)/hexane (50 mL), and the mixture was stirred at room temperature for 20 min. The precipitate was collected by filtration, repeatedly washed 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
  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. additionTo the obtained suspension was added ethyl acetate (25 mL)/hexane (50 mL)
  10. stirringthe mixture was stirred at room temperature for 20 min
  11. filtrationThe precipitate was collected by filtration
  12. washrepeatedly washed with diisopropyl ether/hexane (1:1)
  13. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-42a42adcc6b0429c879ab8ccb68cdc4d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324395B2

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