Ethanol → HCID 67259103, compound

HRID 1467760Notes

Reaction equation

HRID 1467760 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:24]=[CH:23][C:10](/[CH:11]=[N:12]/[C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][O:16][C:17]3=[O:22])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].[CH3:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1.[O-:34][CH2:35][CH3:36].[Na+].C(O)C>C(OCC)(=O)CC>[CH2:1]([N:3]([CH2:6][C:7]1[CH:24]=[CH:23][C:10]([CH:11]2[CH:25]([C:26]3[CH:33]=[CH:32][C:29]([CH3:30])=[CH:28][CH:27]=3)[C:35](=[O:34])[C:36]3[C:18]([C:17]([O:16][CH2:15][CH3:14])=[O:22])=[CH:19][CH:20]=[CH:21][C:13]=3[NH:12]2)=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 77254-MethylbenzaldehydeHCID 2723922Sodium ethoxideHCID 178463922HCID 178463922, compound

Product 1

HCID 67259103HCID 67259103, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (E)-4-(4-((diethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (644 mg, 2 mmol) and 4-methylbenzaldehyde (240 mg, 2 mmol) in ethyl propionate (15 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (138 mg, 6 mmol) in ethanol (5 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hr. 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 crude product, which was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the title compound (320 mg, yield 34%). LC-MS (ESI) m/z: 471 (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 crude product, which
  10. customwas purified by column chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d858f01c43fd4660a9d96027f914f3c4
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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