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Water → HCID 11812072, Verbindung

HRID 377552
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 377552
[CH3:1][S:2][CH2:3][C:4]1[O:9][CH2:8][N:7]([C:10]([CH3:15])([CH3:14])[C:11](O)=[O:12])[C:6](=[O:16])[C:5]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:23][C:24]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:25]=1[NH2:26].O>CN(C)C=O.C(OCC)(=O)C>[F:23][C:24]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:25]=1[NH:26][C:11](=[O:12])[C:10]([N:7]1[C:6](=[O:16])[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([CH2:3][S:2][CH3:1])[O:9][CH2:8]1)([CH3:14])[CH3:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 677752,5-DifluoroanilineHCID 11141777HCID 11141777, Verbindung

Produkt 1

HCID 11812072HCID 11812072, VerbindungAusbeute 7,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

A solution of dicyclohexylcarbodiinide (10.04 g) in N,N-dimethyeformaeide was added to a stirred solution of 2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoic acid (13.00 g) in N,N-dimethylformamide at 20° C. 2,5-Difluoroaniline (7.84 g) was added to the solution at 20° C. and the solution was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with ethyl acetate then added to water and the fine suspension removed by filtration. The organic layer was washed in turn with 0.5M hydrochloric acid, brine, 1.0M sodium carbonate and brine and then dried (magnesium sulphate). The organic solution was evaporated under reduced pressure and the residue was purified by chromatography on silica gel, eluting with dichioromethane to give N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (Compound 3, 1.35 g) as a yellow solid, NMR (CDCl3) 1.68(s,6H), 2.10(s,3H), 3.22(s,2H), 5.30(s,2H), 6.64-6.76(m,1H), 6.95-7.05(m,1H), 7.25-7.38(m,5H), 8.11-8.21(m,2H).

Aufarbeitung

  1. customthe fine suspension removed by filtration
  2. washThe organic layer was washed in turn with 0.5M hydrochloric acid, brine, 1.0M sodium carbonate and brine
  3. dry with materialdried (magnesium sulphate)
  4. customThe organic solution was evaporated under reduced pressure
  5. customthe residue was purified by chromatography on silica gel
  6. washeluting with dichioromethane

Quellen und Nachweise

ORD-Eintrag
ord-bd89b1a2a19545349439ed72b4fdfe9e
Quelldatensatz
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06028032

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