HCID 10564674, compound → HCID 46840871, compound

HRID 1846288Notes

Reaction equation

HRID 1846288 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=[O:5].[OH:21][CH2:22][CH2:23][O:24][C:25]1[C:32]([CH3:33])=[CH:31][C:28]([CH:29]=O)=[CH:27][C:26]=1[CH3:34]>C(O)C.[Cu](Cl)Cl>[OH:21][CH2:22][CH2:23][O:24][C:25]1[C:32]([CH3:33])=[CH:31][C:28]([C:29]2[N:6]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=3)[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:1]=2)=[CH:27][C:26]=1[CH3:34]

Participants

5

Reactant 2

HCID 10564674HCID 10564674, compoundHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

Product 1

HCID 46840871HCID 46840871, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-amino-N-(4-trifluoromethyl-phenyl)-benzamide (0.19 g, 0.68 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.16 g, 0.81 mmol) in anhydrous ethanol (15 mL) was added anhydrous copper (II) chloride (0.273 g, 2.03 mmol). The reaction mixture was stirred at reflux for 16 hours under nitrogen and then cooled to room temperature. Ethanol was evaporated under reduced pressure. The residue was taken in ethyl acetate (100 mL). The organic phase was washed with water (2×75 mL), then brine (75 mL), and dried over anhydrous Na2SO4. Solvent was evaporated; crude compound was purified by column chromatography (silica gel 230-400 mesh; 2:3:5 ethyl acetate, hexanes and CH2Cl2 as eluent) to give the title compound as a white solid. Yield: 0.17 g (55%). MP 160-161° C. 1H-NMR (400 MHz, CDCl3): δ 8.34 (d, J=8.00 Hz, 1H), 7.84-7.82 (m, 2H), 7.62-7.53 (m, 3H), 7.31 (d, J=8.40 Hz, 2H), 6.97 (s, 2H), 3.93-3.89 (m, 2H), 3.80 (t, J=5.20 Hz, 2H), 2.15 (s, 6H), 2.07 (t, J=6.40 Hz, 1H).

Workup

  1. temperatureat reflux for 16 hours under nitrogen
  2. customEthanol was evaporated under reduced pressure
  3. washThe organic phase was washed with water (2×75 mL)
  4. dry with materialbrine (75 mL), and dried over anhydrous Na2SO4
  5. customSolvent was evaporated
  6. customcrude compound was purified by column chromatography (silica gel 230-400 mesh; 2:3:5 ethyl acetate, hexanes and CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-983123adf93e41cc9341f8fc135ea6c3
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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