4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46840873, compound

HRID 1846294Notes

Reaction equation

HRID 1846294 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[OH:23][CH2:24][CH2:25][O:26][C:27]1[C:34]([CH3:35])=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=1[CH3:36]>C(O)C.[Cu](Cl)Cl>[CH:13]([C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[C:18]([O:21][CH3:22])[CH:17]=3)[N:1]=[C:31]2[C:30]2[CH:33]=[C:34]([CH3:35])[C:27]([O:26][CH2:25][CH2:24][OH:23])=[C:28]([CH3:36])[CH:29]=2)=[CH:12][CH:11]=1)([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 2

HCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehydeHCID 86659804HCID 86659804, compound

Product 1

HCID 46840873HCID 46840873, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-N-(4-sec-butyl-phenyl)-5-methoxy-benzamide (0.450 g, 1.51 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.290 g, 1.51 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.610 g, 4.53 mmol). The reaction mixture was stirred at reflux for 4 hours under nitrogen. The solvent was removed and the residue was diluted with dichloromethane (100 mL) and water (100 mL). After separation, the organic phase was further washed with water (100 mL), then brine (100 mL), and dried over sodium sulfate. The crude product was purified by column chromatography on silica gel (230-400 mesh) using hexane/ethyl acetate=1:1 to give the title compound as white solid. Yield: 260 mg (36%). MP 152-154° C. 1H-NMR (400 Hz, CDCl3): δ 7.78 (d, 1H), 7.74 (s. 1H), 7.40 (m, 1H), 7.14 (m, 2H), 7.08 (m, 2H), 6.94 (s, 2H), 3.96 (s, 3H), 3.90 (m, 2H), 3.78 (t, 2H), 2.56 (m, 1H), 2.12 (s, 6H), 2.08 (t, 1H), 1.60 (m, 1H), 1.50 (m, 2H), 1.20 (d, 3H), 0.72 (t, 3H). MS (ES+) m/z: 473.29 (M+1).

Workup

  1. temperatureat reflux for 4 hours under nitrogen
  2. customThe solvent was removed
  3. additionthe residue was diluted with dichloromethane (100 mL) and water (100 mL)
  4. customAfter separation
  5. washthe organic phase was further washed with water (100 mL)
  6. dry with materialbrine (100 mL), and dried over sodium sulfate
  7. customThe crude product was purified by column chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-6935f6b7b6a445669513e5ffd6eca2e3
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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