Ethanol → HCID 67261950, compound

HRID 1968161Notes

Reaction equation

HRID 1968161 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1/[CH:7]=[N:8]/[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][O:12][C:13]2=[O:18].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.[O-:28][CH2:29][CH3:30].[Na+].C(O)C>C(OCC)(=O)CC>[F:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]2([OH:25])[C:29](=[O:28])[C:30]3[C:14]([C:13]([O:12][CH2:11][CH3:10])=[O:18])=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][CH:7]2[C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxideHCID 178480586HCID 178480586, compound

Product 1

HCID 67261950HCID 67261950, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Procedure

To a mixture of (E)-4-((1-methyl-1H-imidazol-2-yl)methyleneamino)isobenzofuran-1(3H)-one (590 mg, 2.4 mmol) and 4-fluorobenzaldehyde (300 mg, 2.4 mmol) in ethyl propionate (20 mL) was added a solution of sodium ethoxide in ethanol [sodium (220 mg, 9.6 mmol) in ethanol (10 mL)]. After the addition, the mixture was stirred at room temperature overnight. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give a crude product, which was purified by flash chromatography to give the title compound (100 mg, yield 10%). LC-MS (ESI) m/z: 410 (M+1)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (10 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate (100 mL×4)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give a crude product, which
  10. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e3e09bf7224a44f7bc1a263d68082d10
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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