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

HRID 75250

反応式

HRID 75250 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1a49b24d67ab4824a2803c129e17254d
出典データセット
uspto-grants-2014_09
特許番号
US08835424B2

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