Ethanol → HCID 67259164, compound

HRID 1467747Notes

Reaction equation

HRID 1467747 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].[Cl: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>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]2[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][CH:11]2[C:10]2[CH:23]=[CH:24][C:7]([CH2:6][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:8][CH:9]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 77264-ChlorobenzaldehydeHCID 2723922Sodium ethoxideHCID 178463922HCID 178463922, compound

Product 1

HCID 67259164HCID 67259164, compoundYield 35%

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 (500 mg, 1.55 mmol) and 4-chlorobenzaldehyde (218 mg, 1.55 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (107 mg, 4.66 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 chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the crude of the title compound (268 mg, yield 35%). LC-MS (ESI) m/z: 491 (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 chromatography (silica gel, petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-1ea7507b306b4ed9bcaabf0ffc99bf47
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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