Benzoyl Peroxide → HCID 135838176, compound

HRID 1654348Notes

Reaction equation

HRID 1654348 reaction equation
[CH3:1][C:2]1[C:3]2[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=2[C:5]2[C:6](=[O:19])[NH:7][C:8]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N:9][C:10]=2[CH:11]=1.[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Br:24][CH2:1][C:2]1[C:3]2[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=2[C:5]2[C:6](=[O:19])[NH:7][C:8]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:15])[CH3:16])=[N:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 135838215HCID 135838215, compound

Product 1

HCID 135838176HCID 135838176, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of N-(6-methyl-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (1.76 g, 5.7 mmoles) in dry benzene (150 ml) was added N-bromosuccinimide (1.01 g, 5.7 mmoles) and dibenzoyl peroxide (15 mg). The mixture was heated to reflux under a nitrogen atmosphere for 2.5 hours. After cooling, benzene was removed under reduced pressure, and the residue was purified on a silica gel column eluting with chloroform to give N-(6-(bromomethyl)-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide as an off-white solid. (1.4 g, 57%) 1H NMR (DMSO-d6, 200 MHz) δ: 1.27(s, 9H, t-butyl); 5.26(s, 2H, CH2Br); 7.63-7.81(m, 3H, Ar); 8.26(dd, J=7.6, 2.0 Hz, 1H, Ar); 9.81(dd, J=7.8, 2.0 Hz, 1H, Ar); 11.27(s, 1H, NH); 12.33(s, 1H, NH). Anal. Calculated for C18H18BrN3O2 : C, 55.68 ; H, 4.67; N, 10.82. Found C, 55.48; H, 4.84; N, 10.57.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for 2.5 hours
  3. temperatureAfter cooling
  4. custombenzene was removed under reduced pressure
  5. customthe residue was purified on a silica gel column
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-f908fcffdd3f4c86aed3056aca495855
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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