Ethyl bromoacetate → Ethyl {3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}acetate

HRID 569824

Reaction equation

HRID 569824 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:19])=[C:4]([F:22])[CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][C:12]([Cl:18])=[CH:13][CH:14]=3)[N:9]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:8]2=[O:19])=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 144237993-(4-bromo-2-fluorobenzyl)-7-chloro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 11431340Ethyl {3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl}acetateYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazoline (500 mg), ethyl bromoacetate (218 mg) and potassium carbonate (360 mg) in N,N-dimethylformamide (5 ml) was stirred at 30° C. for 30 minutes. The solution was evaporated and the residue was dissolved in ethyl acetate. The solution was washed in turn with 0.5N aqueous hydrochloric acid and water, and then dried over magnesium sulfate. The solvent was removed in vacuo to give a crystalline residue, which was crystallized from a mixture of ethyl acetate and n-hexane to give ethyl 2-[3-(4-bromo-2-fluorobenzyl)-7-chloro-1,2,3,4-tetrahydro-2,4-dioxoquinazolin-1-yl]acetate (550 mg).

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed in turn with 0.5N aqueous hydrochloric acid and water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customto give a crystalline residue, which
  7. customwas crystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-7cb180f30f7040a69f7b0f03d3db838d
Source dataset
uspto-grants-1988_03
Patent number
US04734419

Linked notes

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