Water → 2-(1-bromo-ethyl)-3-propyl-3H-quinazolin-4-one

HRID 238195Notes

Reaction equation

HRID 238195 reaction equation
[CH2:1]([C:3]1[N:12]([CH2:13][CH2:14][CH3:15])[C:11](=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:22]Br.O>C(O)(=O)C>[Br:22][CH:1]([C:3]1[N:12]([CH2:13][CH2:14][CH3:15])[C:11](=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 5291112-Ethyl-3-propylquinazolin-4(3H)-one

Product 1

HCID 599931882-(1-bromo-ethyl)-3-propyl-3H-quinazolin-4-oneYield 92.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-ethyl-3-propyl-3H-quinazolin-4-one (125 mg, 0.58 mmol) and sodium acetate (48 mg, 0.58 mmol) in glacial acetic acid (1 mL) cooled in an ice bath was added dropwise a solution of bromine (29.8 μL, 0.58 mmol) in glacial acetic acid (0.5 mL). After addition was complete the reaction was heated to reflux for 2 hours. Water was then added to the solution and the mixture extracted with dichloromethane. The organic layer was then washed with 10% sodium bisulfite solution, water and then dried over magnesium sulfate, filtered and concentrated to yield the product as a brown oil (158 mg, 92%). 1H NMR (CDCl3) δ 1.05 (t, 3H, J=7.3 Hz), 1.66 (m, 1H), 1.91 (m, 1H), 2.19 (d, 3H, J=6.3 Hz), 3.89 (m, 1H,), 4.53 (m, 1H,), 5.04 (q, 1H, J=6.6 Hz), 7.49 (t, 1H, J=7.3 Hz), 7.73 (m, 2H), 8.27 (d, 1H, J=8.4 Hz).

Workup

  1. additionAfter addition
  2. temperaturewas heated
  3. temperatureto reflux for 2 hours
  4. extractionthe mixture extracted with dichloromethane
  5. washThe organic layer was then washed with 10% sodium bisulfite solution, water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e2d342db721c46ff991c6b3dcc6b6e54
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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