Water → (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide

HRID 429494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429494
[CH3:1][NH:2][CH2:3][CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=[CH2:7].O.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:23]([CH:26]2[CH:30]=[N:29][N:28]=[N:27]2)=[CH:22][C:18]=1[C:19](Cl)=[O:20].CO.ClCCl>CC(C)=O.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]([CH2:3][CH:4]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]=[CH2:7])[C:19](=[O:20])[C:18]1[CH:22]=[C:23]([C@H:26]2[CH:30]=[N:29][N:28]=[N:27]2)[CH:24]=[CH:25][C:17]=1[O:16][CH3:15]

Komponenten

7

Edukt 4

HCID 962WaterHCID 18354441N-methyl-(2-phenylpent-4-enyl)amineHCID 183544512-methoxy-5-(4H-triazol-4-yl)benzoyl chlorideHCID 21226129Dichloromethane methanol

Produkt 1

HCID 69775799(S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel2×

Versuchsvorschrift

Combine N-methyl-(2-phenylpent-4-enyl)amine (1.00 g, 5.7 mmol), acetone (50 mL), water (20 mL), and sodium bicarbonate (0.3 g, 2.85 mmol). Add portionwise, a solution of 2-methoxy-5-(4H-triazol-4-yl)benzoyl chloride (1.4 g, 6.3 mmol) in acetone (50 mL). After 10 hours, dilute the reaction mixture with a saturated aqueous sodium bicarbonate solution and evaporate in vacuo to remove most of the acetone. Extract five times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane to give (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide: Rf=0.25 (silica gel, 5% methanol/dichloromethane).

Aufarbeitung

  1. additionAdd portionwise
  2. customevaporate in vacuo
  3. customto remove most of the acetone
  4. extractionExtract five times with dichloromethane
  5. dry with materialDry the combined organic layers over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-44c6264170524737991b7d860f206cd1
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316445B1

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