4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → HCID 46840872, compound

HRID 1846291Notes

Reaction equation

HRID 1846291 reaction equation
[NH2:1][C:2]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[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:25][CH2:26][CH2:27][O:28][C:29]1[C:36]([CH3:37])=[CH:35][C:32]([CH:33]=O)=[CH:31][C:30]=1[CH3:38]>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][C:19]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:18][CH:17]=3)[N:1]=[C:33]2[C:32]2[CH:35]=[C:36]([CH3:37])[C:29]([O:28][CH2:27][CH2:26][OH:25])=[C:30]([CH3:38])[CH:31]=2)=[CH:12][CH:11]=1)([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 2

HCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehydeHCID 67461929HCID 67461929, compound

Product 1

HCID 46840872HCID 46840872, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-N-(4-sec-butyl-phenyl)-4-methanesulfonyl-benzamide (0.20 g, 0.55 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.13 g, 0.66 mmol) in ethanol (15 mL) was added anhydrous copper (II) chloride (0.222 g, 1.65 mmol). The resulting mixture was stirred at reflux for 24 hours and the solvent was removed using a rotary evaporator. The residue was then diluted with water (50 mL), extracted with ethyl acetate (2×100 mL), and concentrated on using a rotary evaporator. The crude product was made into a slurry in diethyl ether (20 mL) and filtered to provide the title compound as white solid. Yield: 0.20 g (70%). MP 235-237° C. 1H-NMR (400 MHz, CDCl3): δ 8.53 (d, 1H), 8.41 (d, 1H), 8.00 (dd, 1H), 7.16 (d, 2H), 7.06 (d, 2H), 7.00 (s, 2H), 3.91 (m, 2H), 3.80 (m, 2H), 3.15 (s, 3H), 2.59 (m, 1H), 2.13 (s, 6H), 2.04 (m, 1H), 1.58 (m, 2H), 1.22 (d, 3H), 0.73 (t, 3H). MS (ES+) m/z: 521.22 (M+1).

Workup

  1. temperatureat reflux for 24 hours
  2. customthe solvent was removed
  3. customa rotary evaporator
  4. additionThe residue was then diluted with water (50 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. concentrationconcentrated
  7. customa rotary evaporator
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5a83dbe93dc041cd90d60cbc8c93ff9b
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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