Benzaldehyde → HCID 67261824, compound

HRID 1968129Notes

Reaction equation

HRID 1968129 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:18]=[C:17]2[C:13]([CH2:14][O:15][C:16]2=[O:19])=[C:12](/[N:20]=[CH:21]/[C:22]2[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=2)[CH:11]=1.[O-:28][CH2:29][CH3:30].[Na+].C(O)C>C(OCC)(=O)CC>[F:9][C:10]1[CH:18]=[C:17]([C:16]([O:15][CH2:14][CH3:13])=[O:19])[C:30]2[C:29](=[O:28])[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:21]([C:22]3[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=3)[NH:20][C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 2723922Sodium ethoxideHCID 178480587HCID 178480587, compound

Product 1

HCID 67261824HCID 67261824, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of benzaldehyde (212 mg, 2 mmol) and (E)-6-fluoro-4-((1-methyl-1H-imidazol-2-yl)methyleneamino)isobenzofuran-1(3H)-one (518 mg, 2 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (184 mg, 8 mmol) in ethanol (5 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 0.5 hr. The mixture was quenched with water (20 mL) and solvent was removed in vacuum. The residue was dissolved in water and extracted with ethyl acetate three times. The combined organic layers were washed by water and brine, and then evaporated to dryness, the crude product was purified by chromatography to obtain a yellow solid. The solid was dried in vacuum at 50° C. to give the title compound (250 mg, yield 32%). LC-MS (ESI) m/z: 394 (M+1)+.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with water (20 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate three times
  6. washThe combined organic layers were washed by water and brine
  7. customevaporated to dryness
  8. customthe crude product was purified by chromatography
  9. customto obtain a yellow solid
  10. customThe solid was dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-fe2485ffb50741cf90fe50c992463c34
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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