Water → HCID 21958885, compound

HRID 1828751Notes

Reaction equation

[Br:1]Br.[CH2:3]([N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]1[CH2:21][CH2:22][CH3:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH2:3]([N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]1[CH:21]([Br:1])[CH2:22][CH3:23])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Bromine (1.9 g, 12 mmol, 1.2 equiv.) was added dropwise to a stirred solution of 3-benzyl-2-propylquinazolin-4(3H)-one (1–2, 2.78 g, 10.0 mmol, 1 equiv.) and sodium acetate(0.98 g, 12 mmol, 1.2 equiv.) in acetic acid (10 mL). The reaction was warmed at 45° C. for 2 hours and then poured into water (300 mL). The resulting mixture was stirred for 2 hours and the solid collected by filtration to provide 3-benzyl-2(1-bromopropyl)quinazolin-4(3H)-one (1–3) as an off-white solid. 1H NMR (500 MHz, CDCl3)δ8.35 (d, J=7 Hz, 1H), 7.64 (m, 2H), 7.53 (t, J=7 Hz, 1H), 7.33 (m, 2H), 7.28 (m, 1H), 7.15 (d, J=7 Hz, 2H), 6.22 (d, J=16 Hz, 1H), 4.95 (d, J=16 Hz, 1H), 4.64 (t, J=7 Hz, 1H), 2.48 (m, 1H), 2.25 (m, 1H), 0.77 (t, J=7 Hz, 3H).

Workup

filtrationthe solid collected by filtration

Sources & evidence

ORD record: ord-c05728de205647559b457e176a021b85
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060705B2

Reaction notes

Loading…