Triethylamine → 3,5-dichlorophenyl 2-methyl-2-(6-methyl-5-phenyl-2 3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionate

HRID 1600533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600533
[CH3:1][C:2]([N:7]1[C:12](=[O:13])[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:10]([CH3:20])[O:9][CH2:8]1)([CH3:6])[C:3]([OH:5])=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:40][C:41]1[CH:42]=[C:43](O)[CH:44]=[C:45]([Cl:47])[CH:46]=1.C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:6][C:2]([N:7]1[C:12](=[O:13])[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:10]([CH3:20])[O:9][CH2:8]1)([CH3:1])[C:3]([O:5][C:43]1[CH:42]=[C:41]([Cl:40])[CH:46]=[C:45]([Cl:47])[CH:44]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 115713,5-DichlorophenolHCID 11776TriphenylphosphineHCID 22118282HCID 22118282, Verbindung

Produkt 1

HCID 218298983,5-dichlorophenyl 2-methyl-2-(6-methyl-5-phenyl-2 3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionateAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22996148Carbon tetrachloride methylene chlorideLösungsmittel

Versuchsvorschrift

To a suspension of 2-methyl-2-(6-methyl-5-phenyl-2,3-dihydro-4-oxo-4H-1,3-oxazin-3-yl)-propionic acid (1.1 g) in 14 ml of CCl4 --CH2Cl2 (1:1) was added triphenylphosphin (1.38 g), then the mixture was refluxed for 40 min. The reaction mixture was ice-cooled and 3,5-dichlorophenol (0.65 g) and triethylamine (0.4 g) were slowly added, then it was stirred at room temperature for 1 h. After evaporation of the solvent, the residue was dissolved in ethyl acetate. The insolubles were filtered off and the filtrate was evaporated. The residue was purified by chromatography on a silica gel column to get the captioned compound (0.7 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 40 min
  2. temperaturecooled
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. filtrationThe insolubles were filtered off
  6. customthe filtrate was evaporated
  7. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-bcb15fa2d0de4348bc656e727e5cba34
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977025

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