Phenethylamine → 5-chloro-2-methoxy-N-(2-phenylethyl)benzamide

HRID 2266401

Reaktionsgleichung

Reaktionsgleichung von HRID 2266401
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([CH:19]=1)[C:16](O)=[O:17].C(N(CC)CC)C.F[B-](F)(F)F.C(OC(C(=NOC(N(C)C)=[N+](C)C)C#N)=O)C>CN(C)C=O.C(OCC)(=O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15]([CH:19]=1)[C:16]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:17]

Komponenten

7

Edukt 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 769705-Chloro-o-anisic acidHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 1185755-chloro-2-methoxy-N-(2-phenylethyl)benzamideAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.0 g phenethylamine, 5.0 g 5-chloro-2-methoxy-benzoic acid, and 2.72 ml triethylamine were dissolved in 100 ml dimethylformamide. 8.80 g O-((Ethoxycarbonyl)cyanomethyleneamino)-N,N,N′,N′-tetramethyluronium tetrafluoroborate were added portionwise. The reaction mixture is stirred at room temperature for three hours. 300 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and then the solvent was removed in vacuo to obtain 6.5 g 5-Chloro-2-methoxy-N-phenethyl-benzamide.

Aufarbeitung

  1. washthe mixture was washed three times with portions of 50 ml saturated NaHCO3 solution and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1e9175463bb945c39c9c4b4ecdec82de
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858647B2

Verknüpfte Notizen

Wird geladen…