alpha-Methylcinnamoylchloride → (+/-)-(E)-2-methyl-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]-3-phenyl-2-propenamide

HRID 349396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349396
[CH3:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](Cl)=[O:4].[CH3:13][CH:14]([CH3:28])[CH:15]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[N:16]1[CH:20]=[N:19][CH:18]=[N:17]1>C(Cl)Cl.N1C=CC=CC=1>[CH3:1]/[C:2](=[CH:6]\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)/[C:3]([NH:27][C:24]1[CH:25]=[CH:26][C:21]([CH:15]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:14]([CH3:28])[CH3:13])=[CH:22][CH:23]=1)=[O:4]

Komponenten

5

Edukt 2

HCID 230201alpha-MethylcinnamoylchlorideHCID 10900053(+/-)-4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-benzenamine

Produkt 1

HCID 9885242(+/-)-(E)-2-methyl-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]-3-phenyl-2-propenamideAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-methyl-3-phenyl-2-propenoyl chloride (0.0554 mol) in CH2Cl2 (50 ml) was added dropwise to a solution of (±)-4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-benzenamine (0.037 mol) in pyridine (8 ml) and CH2Cl2 (100 ml) and the mixture was stirred at RT for 4 hours. The solvent was evaporated and the residue was taken up in water/EtOAc. The organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.1). The pure fractions were collected and evaporated. The residue was crystallized from (C2H5)2O/methylethylketone, yielding 2.7 g (21%) of (±)-(E)-2-methyl-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]phenyl]-3-phenyl-2-propenamide (compound 154).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.1)
  6. customThe pure fractions were collected
  7. customevaporated
  8. customThe residue was crystallized from (C2H5)2O/methylethylketone

Quellen und Nachweise

ORD-Eintrag
ord-379dc236aaca45829bf2d35af7edf493
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179825B2

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