2-amino-N-(4-isopropylphenyl)benzamide → HCID 46841009, compound

HRID 1846308Notes

Reaction equation

HRID 1846308 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[OH:20][CH2:21][CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][C:27]([CH:28]=O)=[CH:26][C:25]=1[CH3:33]>C(O)C.[Cu](Cl)Cl>[OH:20][CH2:21][CH2:22][O:23][C:24]1[C:31]([CH3:32])=[CH:30][C:27]([C:28]2[N:6]([C:7]3[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=3)[C:4](=[O:5])[C:3]3[C:2](=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:1]=2)=[CH:26][C:25]=1[CH3:33]

Participants

5

Reactant 2

HCID 28065462-amino-N-(4-isopropylphenyl)benzamideHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

Product 1

HCID 46841009HCID 46841009, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-N-(4-isopropylphenyl)benzamide (0.400 g, 1.57 mmol) and 4-(2-hydroxyethoxy)-3,5-dimethylbenzaldehyde (0.30 g, 1.57 mmol) in anhydrous ethanol (20 mL) was added anhydrous copper (II) chloride (0.63 g, 4.71 mmol). The reaction mixture was stirred at reflux for 4 hours under nitrogen. The solvent was removed and the residue was diluted with dichloromethane (150 mL) and water (100 mL). The organic phase was separated and further washed with water (100 mL), brine (100 mL), and dried over sodium sulfate. The crude mixture was purified by column chromatography on silica gel (230-400 mesh) using hexane/ethyl acetate (1:1) as eluent to give the title compound as a white solid. Yield: 100 mg (15.6%). MP 160-162° C. 1H-NMR (400 Hz, CDCl3): δ 8.34 (d, J=7.6 Hz, 1H), 7.80 (m, 2H), 7.52 (m, 1H), 7.17 (d, J=8.4 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 6.97 (s, 2H), 3.90 (m, 2H), 3.78 (t, J=4.8 Hz, 2H), 2.86 (m, 1H), 2.13 (s, 6H), 2.06 (t, J=6.4 Hz, 1H), 1.20 (d, J=7.2 Hz, 3H). MS (ES+) m/z: 429.52 (M+1).

Workup

  1. temperatureat reflux for 4 hours under nitrogen
  2. customThe solvent was removed
  3. additionthe residue was diluted with dichloromethane (150 mL) and water (100 mL)
  4. customThe organic phase was separated
  5. washfurther washed with water (100 mL), brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe crude mixture was purified by column chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-5379a414644f4ef791f40c634ade8849
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…