N-bromobutanimide → 4-(3-acetoxyphenyl)-7-bromomethyl-1-isopropyl-2(1H)-quinazolinone

HRID 461774Notes

Reaction equation

HRID 461774 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[N:14]([CH:22]([CH3:24])[CH3:23])[C:13](=[O:25])[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Br:26]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([CH2:21][Br:26])=[CH:18][CH:19]=3)[N:14]([CH:22]([CH3:23])[CH3:24])[C:13](=[O:25])[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 203719573-[7-Methyl-2-oxo-1-(propan-2-yl)-1,2-dihydroquinazolin-4-yl]phenyl acetate

Product 1

HCID 213925084-(3-acetoxyphenyl)-7-bromomethyl-1-isopropyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 14 g of 4-(3-acetoxyphenyl)-1-isopropyl-7-methyl-2(1H)-quinazolinone, 20 g of N-bromosuccinimide, and 600 ml of carbon tetrachloride is irradiated with infrared light for 15 minutes in a 1000 ml flat-bottom flask while stirring and refluxing. After cooling to room temperature with an ice bath, the mixture is washed successively with 500 ml and 100 ml of water in a 2 liter separatory funnel. Each water phase is washed with an additional 100 ml of carbon tetrachloride. The combined carbon tetrachloride phase is evaporated to dryness. The resulting residue is dissolved in 200 ml of methanol and evaporated to dryness to obtain crude 4-(3-acetoxyphenyl)-7-bromomethyl-1-isopropyl-2(1H)-quinazolinone. A thin-layer chromatogram on Silica Gel GE with ethyl acetate as the mobile phase shows the presence of the desired monobrominated product and dibrominated by-product.

Workup

  1. customis irradiated with infrared light for 15 minutes in a 1000 ml flat-bottom flask
  2. temperaturerefluxing
  3. washthe mixture is washed successively with 500 ml and 100 ml of water in a 2 liter separatory funnel
  4. washEach water phase is washed with an additional 100 ml of carbon tetrachloride
  5. customThe combined carbon tetrachloride phase is evaporated to dryness
  6. dissolutionThe resulting residue is dissolved in 200 ml of methanol
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-6e17731a442d4cc8a6a12f740b6a7572
Source dataset
uspto-grants-1977_12
Patent number
US04064246

Reaction notes

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