Ethanol → 3-(3-fluoro-4-methoxyphenyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 2241226Notes

Reaction equation

HRID 2241226 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([F:14])[CH:7]=1.[C:19](Cl)(Cl)=[O:20].CCO>C1(C)C=CC=CC=1>[F:14][C:8]1[CH:7]=[C:6]([N:5]2[CH2:4][C:3]3[C:2](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:1][C:19]2=[O:20])[CH:11]=[CH:10][C:9]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 6371PhosgeneHCID 66385653N-(2-aminobenzyl)-3-fluoro-4-methoxyaniline

Product 1

HCID 685164283-(3-fluoro-4-methoxyphenyl)-3,4-dihydroquinazolin-2(1H)-oneYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of crude N-(2-aminobenzyl)-3-fluoro-4-methoxyaniline (246 mg, 1 mmol) in 10 mL toluene at 0° C. under a drying tube was added phosgene solution (20% in toluene, 683 μL, 1.30 mmol). The cooling bath was removed and the reaction allowed to warm to room temperature over 30 minutes. The solution was then warmed to reflux. After 1 hour, the reaction was concentrated to dryness and the residue dissolved in a minimum of hot 95% EtOH. A precipitate formed which was isolated by filtration with 95% EtOH and dried to give a tan solid (65 mg, 24%). 1H NMR (400 MHz, CDCl3) δ 7.23 (m, 1H), 7.14 (m, 1H), 7.08 (m, 2H), 7.01 (m, 2H), 6.81 (d, 1H), 4.80 (s, 2H), 3.91 (s, 3H).

Workup

  1. customThe cooling bath was removed
  2. temperatureThe solution was then warmed to reflux
  3. concentrationthe reaction was concentrated to dryness
  4. dissolutionthe residue dissolved in a minimum of hot 95% EtOH
  5. customA precipitate formed which
  6. customdried

Sources & evidence

ORD record
ord-8ed7c7009ddd48a3a07715c682d3e0be
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…