Benzenamine, 2-bromo-4-nitro- → 3-(2-Bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione

HRID 562690

Reaktionsgleichung

Reaktionsgleichung von HRID 562690
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)=[C:2]=[O:3].[Br:14][C:15]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:16]=1[NH2:17].CCN(C(C)C)C(C)C.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[Br:14][C:15]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:16]=1[N:17]1[C:6](=[O:8])[C:5]2[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:1][C:2]1=[O:3]

Komponenten

6

Edukt 4

HCID 25840Benzenamine, 2-bromo-4-nitro-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 519494Methyl 2-isocyanatobenzoate

Produkt 1

HCID 220644013-(2-Bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dioneAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-isocyanatobenzoate (0.266 g, 1.5 mmol) and 2-bromo-4-nitroaniline (0.325 g, 1.5 mmol) in DMF (2 mL) was added DIEA (0.79 mL). The reaction mixture was stirred at room temp for 24 hr, with addition of DBU (0.22 mL) at 17 hr. The reaction mixture was extracted with EtOAc, washed with 1 N HCl and brine, dried and concentrated to give crude product, which was chromatographed on silica gel with 10% EtOAc/CH2Cl2 to give 3-(2-bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione (0.24 g, 44%). ES-MS (M+H)+=362, 364 (Br).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washwashed with 1 N HCl and brine
  3. customdried
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customwas chromatographed on silica gel with 10% EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-8094c4135b0c4c9196cdcc72529eb6d2
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067428B2

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