Lawesson's reagent → 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thione

HRID 1509300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509300
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=O)[CH2:8][O:7][C:6]=2[N:12]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=[S:28])[CH2:8][O:7][C:6]=2[N:12]=1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Produkt 1

HCID 866836666-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazine-2(3H)-thioneAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (0.26 g, 0.852 mmol) and Lawesson's Reagent (0.34 g, 0.852 mmol) in toluene (10 ml) was heated at 120 degree for 16 h. The reaction mixture was concentrated to dryness and was added DCM (5 ml) and diisopropyl ether (20 ml). The precipitate was filtered to give product (0.18 g). 1H NMR (500 MHz, DMSO-d6): 12.9 (br, 1H), 7.35-7.55 (m, 5H), 7.32 (s, 1H), 5.16 (s, 2H).

Aufarbeitung

  1. temperaturewas heated at 120 degree for 16 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additionwas added DCM (5 ml) and diisopropyl ether (20 ml)
  4. filtrationThe precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-08875d6b041a4cb9b8c13ac7f0128d39
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221838B2

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