Imidazole → HCID 136375566, compound

HRID 374770Notes

Reaction equation

HRID 374770 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[C:11]([CH3:19])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].II.[NH:32]1[CH:36]=[CH:35][N:34]=[CH:33]1>[Cu].O.CN1CCCC1=O>[NH:32]1[CH:36]=[CH:35][N:34]=[C:33]1[C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[C:11]([CH3:19])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11430Potassium CarbonateHCID 136110484HCID 136110484, compound

Product 1

HCID 136375566HCID 136375566, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A stirred mixture of 2-(5-bromo-2-n-propoxyphenyl)-8-methylquinazolin-4(3H)-one (Preparation 11; 0.6 g, 0.0016 mol), anhydrous potassium carbonate (0.22 g, 0.0016 tool), copper bronze (0.1 g, 0.0016 mol), iodine (0.051 g, 0.004 mol), imidazole (0.55 g, 0.008 mol) and 1-methyl-2-pyrrolidinone (20 ml) was heated at 180° C. under a nitrogen atmosphere for 6 hours. The mixture was cooled and poured into water (150 ml), then the resulting mixture extracted with a dichloromethane-methanol mixture (9:1, 4×40 ml ). The organic extracts were combined, dried (Na2SO4) and evaporated under vacuum. The semi-solid residue was chromatographed on silica gel (10 g) using a methanol in dichloromethane elution gradient (0-4% ). Evaporation of the appropriate fractions gave the title compound which crystallized from ethyl acetate as colorless needles (0.016 g, 3%); Rf 0.5 (silica; dichloromethane-methanol 95:5).

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe resulting mixture extracted with a dichloromethane-methanol mixture (9:1, 4×40 ml )
  3. dry with materialdried (Na2SO4)
  4. customevaporated under vacuum
  5. customThe semi-solid residue was chromatographed on silica gel (10 g)
  6. washa methanol in dichloromethane elution gradient (0-4% )
  7. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-035b57eeb881459eb8dd2eafc0899bb3
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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