Water → HCID 10812631, compound

HRID 617223Notes

Reaction equation

HRID 617223 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([CH2:16][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[N:8]=[C:7]2[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1.[O-]CC.[Na+].[CH:50]([C:52]1[N:53]([CH3:57])[CH:54]=[CH:55][N:56]=1)=O.O>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9](/[CH:16]=[CH:50]/[C:52]1[N:53]([CH3:57])[CH:54]=[CH:55][N:56]=1)[N:8]=[C:7]2[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[C:38]([O:44][CH3:45])[CH:37]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2723922Sodium ethoxideHCID 10722756HCID 10722756, compound

Product 1

HCID 10812631HCID 10812631, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

[6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazolin-2- yl]methyltriphenylphosphonium chloride (9.1 g) was added at room temperature to a solution of sodium ethoxide in ethanol (prepared from Na (0.394 g) and ethanol (100 ml)). Then a solution of 2-formyl-l-methylimidazole (1.7 g) in ethanol (10 ml) was added dropwise. The mixture was stirred at room temperature for 3 hours, poured into water and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4), and the solvent was distilled off. The residue was subjected to column chromatography on silica gel. From the fraction eluted with chloroform/methanol (20:1, v/v), (E)-6,7-dimethoxy-4-(3,4-dimethoxy- phenyl)-2-[2-(1-methylimidazol-2-yl)vinyl]quinazoline (5.1 g, 82%) was obtained and recrystallized from ethanol/chloroform.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off
  5. washFrom the fraction eluted with chloroform/methanol (20:1

Sources & evidence

ORD record
ord-526241fff5bb488e862fb8eb3a808bd4
Source dataset
uspto-grants-1999_09
Patent number
US05948782

Reaction notes

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