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

HRID 1435803노트

반응식

[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

참가 물질

반응물 2

HCID 7412Benzoyl chloride

HCID 798582-Amino-5-bromobenzoic acid

생성물 1

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

실험 절차

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).

후처리

customthe crystals that formed
filtrationwere collected by filtration
washwere washed with hexanes

출처 및 근거

ORD 기록: ord-4600d3862d0b4b4caf676671d40f5734
출처 데이터셋: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07618958B2

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