Ethanol → HCID 67261714, compound

HRID 1968112Notes

Reaction equation

HRID 1968112 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]=[CH:14][N:13]=[C:12]1/[CH:16]=[N:17]/[C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH2:20][O:21][C:22]2=[O:27].[O-:28][CH2:29][CH3:30].[Na+].C(O)C>C(OCC)(=O)CC>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[C:29](=[O:28])[C:30]3[C:23]([C:22]([O:21][CH2:20][CH3:19])=[O:27])=[CH:24][CH:25]=[CH:26][C:18]=3[NH:17][CH:16]2[C:12]2[N:11]([CH3:10])[CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

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

Product 1

HCID 67261714HCID 67261714, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of compound 4-fluorobenzaldehyde (248 mg, 2 mmol) and (E)-4-((1-methyl-1H-imidazol-2-yl)methyleneamino)isobenzofuran-1(3H)-one (482 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, washed with water and brine, and then concentrated to give the crude product, which was purified by column chromatography to obtain a yellow solid (200 mg, yield 25%). 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. washwashed with water and brine
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-3352681b3b8b456a9cc8e0d978ae4261
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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