Potassium Carbonate → Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate

HRID 1446875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446875
[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 133148194-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol

Produkt 1

HCID 13314823Ethyl 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol (0.00255 mol, 0.7 g, prepared as above), ethyl 2-bromopropionate (0.00255 mol, 0.46 g) and potassium carbonate (0.00255 mol, 0.35 g) were mixed in methyl ethyl ketone (5 ml) and heated under reflux for 6 hours. The solvent was then evaporated, the residue taken into water (25 ml) and twice extracted with diethyl ether (25 ml). An oily residue was obtained which was purified by preparative thin layer chromatography on silica gel, eluent toluene/diethyl ether. Yield 0.75 g, mp 68.0°-68.6° C.; ir, and pmr spectra and analysis consistent with assigned structure.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was then evaporated
  4. extractiontwice extracted with diethyl ether (25 ml)
  5. customAn oily residue was obtained which
  6. customwas purified by preparative thin layer chromatography on silica gel, eluent toluene/diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ccd6d813fe9945f8847a0f6dcac28dc2
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04314065

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