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

HRID 1435803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435803
[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%): mp: 199-201° C.; 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-4600d3862d0b4b4caf676671d40f5734
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618958B2

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