Bromine → HCID 59993195, compound

HRID 238200Notes

Reaction equation

HRID 238200 reaction equation
[CH2:1]([C:3]1[N:12]([CH3:13])[C:11](=[O:14])[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:20]Br>C(O)(=O)C>[Br:20][CH:1]([C:3]1[N:12]([CH3:13])[C:11](=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 3253524-Quinazolone, 2-ethyl-3-methylHCID 517045Sodium Acetate

Product 1

HCID 59993195HCID 59993195, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-ethyl-3-methyl-3H-quinazolin-4-one (11.28 g, 60 mmol) and sodium acetate (4.92 g, 60 mmol) in glacial acetic acid (130 mL) heated to 50° C. was added dropwise a solution of bromine (3.70 mL, 72 mmol) in glacial acetic acid (50 mL). After addition was complete the reaction was heated to reflux for 2 hours. The reaction was then cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 10% sodium bisulfite solution, water and dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (0-25% ethyl acetate-hexanes) to yield the product as a white solid (12.68 g, 79%). 1H NMR (400 MHz, CDCl3) δ 2.19 (d, 3H, J=6.6 Hz), 3.77 (s, 3H), 5.08 (q, 1H, J=6.6 Hz), 7.50 (t, 1H, J=8.1 Hz), 7.74 (m, 2H), 8.29 (d, 1H, J=8.9 Hz); ESI-MS m/z 267.0 (M+1)+.

Workup

  1. additionAfter addition
  2. temperaturewas heated
  3. temperatureto reflux for 2 hours
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 10% sodium bisulfite solution, water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by column chromatography (0-25% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-f77175df679a418093f0a1af8d74551c
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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