Water → HCID 44608067, Verbindung

HRID 1943659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943659
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[N:11][C:6]2[O:7][CH2:8][CH2:9][NH:10][C:5]=2[CH:4]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([Br:27])[C:24]=1[O:25][CH3:26])[C:19](Cl)=[O:20].C(N(CC)CC)C.O>ClCCl>[Br:15][C:16]1[CH:17]=[C:18]([C:19]([N:10]2[CH2:9][CH2:8][O:7][C:6]3[N:11]=[CH:12][C:3]([C:2]([F:13])([F:1])[F:14])=[CH:4][C:5]2=3)=[O:20])[CH:22]=[C:23]([Br:27])[C:24]=1[O:25][CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 669366917-Trifluoromethyl-2,3-dihydro-1H-pyrido[2,3-B][1,4]oxazine

Produkt 1

HCID 44608067HCID 44608067, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 5 ml flask, 7-trifluoromethyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (27 mg, 0.23 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (65 mg, 0.20 mmol) were dissolved in dichloromethane (0.6 ml), and then triethylamine (0.55 ml, 0.33 mmol) was added thereto dropwise at 0□. After stirring for 4 hours at room temperature, water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of methanol:dichloromethane=1:100. The fractions containing the product were collected and evaporated to obtain white solid (64 mg, 98%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with a solvent of methanol
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-35914bf01d7b47eb9e6e2d6f3352906a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394792B2

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