Benzoyl chloride → 6-bromo-2-phenyl-4H-benzo[d][1,3]oxazin-4-one

HRID 75250

Reaktionsgleichung

Reaktionsgleichung von HRID 75250
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[Br:11][C:8]1[CH:9]=[CH:10][C:2]2[N:1]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Komponenten

3

Edukt 2

HCID 7412Benzoyl chlorideHCID 798582-Amino-5-bromobenzoic acid

Produkt 1

HCID 3504116-bromo-2-phenyl-4H-benzo[d][1,3]oxazin-4-oneAusbeute 97,4 %

Versuchsvorschrift

The 2-amino-5-bromobenzoic acid (5 g, 23.1 mmol) was treated with benzoyl chloride (237 mL, 2.04 mol) at 140° C. for 3 h. After the reaction mixture was cooled to rt, the crystals that formed were collected by filtration and were washed with hexanes to provide 64 as light brown needles (6.8 g, 97%): 1H NMR (CDCl3) δ 7.51-7.2 (m, 4H), 7.9 (dd, 1H, J=2.3, 8.6 Hz), 8.30-8.33 (m, 2H), 8.8 (d, 1H, J=2.2 Hz); 13C NMR (CDCl3) δ 158.19, 157.35, 145.75, 139.58, 132.82, 130.97, 129.77, 128.82, 128.73, 128.29, 121.37, 118.27; MS (EI) m/e (relative intensity) 303 (M+, 36), 301 (M+, 36), 259 (14), 257 (14), 226 (6), 224 (6), 178 (9), 170 (9), 168 (9), 151 (4), 105 (100).

Aufarbeitung

  1. customthe crystals that formed
  2. filtrationwere collected by filtration
  3. washwere washed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1a49b24d67ab4824a2803c129e17254d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835424B2

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