Water → HCID 10812631, compound

HRID 1458913Notes

Reaction equation

HRID 1458913 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-1-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 over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform/methanol (20/1, v/v) gave (E)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[2-(1-methylimidazol-2-yl)vinyl]quinazoline (5.1 g, 82%) which was then recrystallized from ethanol-chloroform.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated
  5. washThe fractions eluted with chloroform/methanol (20/1

Sources & evidence

ORD record
ord-55975af9b2e249a08ec6174d3c658b8e
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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