Benzoyl Peroxide → HCID 19744051, compound

HRID 2254061Notes

Reaction equation

HRID 2254061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:19]3[C:14](=[CH:15][C:16]([CH3:20])=[CH:17][CH:18]=3)[C:13](=[O:21])[N:12]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:11]2=[O:28])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:29]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:10]([CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[C:11](=[O:28])[N:12]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]2=[O:21]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53733030HCID 53733030, compound

Product 1

HCID 19744051HCID 19744051, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In 30 ml of carbon tetrachloride were refluxed 3.5 g of ethyl 1-(3,4-dichlorophenyl)methyl-1,4-dihydro-2,4-dioxo-6-methyl-3(2H)-quinazolineacetate, 1.66 g of N-bromosuccinimide and calalytic amount of benzoyl peroxide for 2 hours. The insolubles were filtered off and the filtrate was concentrated. Ether was added to the residue for crystallization and the crystals thus obtained were recrystallized from acetonitrile to obtain 2.0 g of ethyl 6-bromomethyl-1 -(3,4-dichlorophenyl)methyl-1,4-dihydro-2,4-dioxo-3(2H)-quinazolineacetate. m.p. 128°-129° C.

Workup

  1. filtrationThe insolubles were filtered off
  2. concentrationthe filtrate was concentrated
  3. additionEther was added to the residue for crystallization
  4. customthe crystals thus obtained
  5. customwere recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b53ed6d713f64d10ba1dca364c3909c0
Source dataset
uspto-grants-1993_08
Patent number
US05234928

Reaction notes

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