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

HRID 1243891Notes

Reaction equation

HRID 1243891 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 3504116-bromo-2-phenyl-4H-benzo[d][1,3]oxazin-4-oneYield 97.4%

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1b68941f85154e74aeb16bf8669c2008
Source dataset
uspto-grants-2006_10
Patent number
US07119196B2

Reaction notes

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