Bromine → HCID 136110484, compound

HRID 374784Notes

Reaction equation

HRID 374784 reaction equation
BrBr.[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:21][CH2:22][CH3:23])[NH:10][C:9]2=[O:24].[Br:25]N1C(=O)CCC1=O>C(O)(=O)C.CN(C)C=O>[Br:25][C:18]1[CH:17]=[CH:16][C:15]([O:20][CH2:21][CH2:22][CH3:23])=[C:14]([C:11]2[NH:10][C:9](=[O:24])[C:8]3[C:13](=[C:4]([CH3:3])[CH:5]=[CH:6][CH:7]=3)[N:12]=2)[CH:19]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 67184N-bromobutanimideHCID 136029836HCID 136029836, compound

Product 1

HCID 136110484HCID 136110484, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

Bromine (3.2 g, 0.020 mol) was added dropwise to a stirred solution of 8-methyl-2-(2-n-propoxyphenyl)quinazolin-4(3H)-one (3 g, 0.010 mol) in glacial acetic acid (45 ml) at 95° C. The resulting suspension was heated at 105° C. for 18 hours and then evaporated under vacuum. The resulting solid was dissolved in dimethylformamide (25 ml) and the stirred solution treated dropwise with a solution of N-bromosuccinimide (0.89 g, 0.0051 mol) in dimethylformamide (25 ml). After 1 hour at ambient temperature, the solvent was evaporated under vacuum and the residue dissolved in ethyl acetate (50 ml). This solution was washed with saturated aqueous sodium carbonate solution (50 ml), dried-(Na2SO4) and evaporated under vacuum. The residue was chromatographed on silica gel (30 g) using a methanol in dichloromethane elution gradient (0-100%) to give the title compound as a white solid (1.67 g, 45%), m.p. 179°-180° C.; Rf 0.7 (silica; dichloromethanemethanol; 99:1). This material was used without any further purification.

Workup

  1. customevaporated under vacuum
  2. dissolutionThe resulting solid was dissolved in dimethylformamide (25 ml)
  3. customthe solvent was evaporated under vacuum
  4. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  5. washThis solution was washed with saturated aqueous sodium carbonate solution (50 ml), dried-(Na2SO4) and
  6. customevaporated under vacuum
  7. customThe residue was chromatographed on silica gel (30 g)
  8. washa methanol in dichloromethane elution gradient (0-100%)

Sources & evidence

ORD record
ord-586ff75cfb534162a223795b4bf470aa
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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