Hydrochloric Acid → HCID 57879353, compound

HRID 1673375Notes

Reaction equation

HRID 1673375 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([NH:17][CH:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]1(Br)[C:20]([O:22][CH3:23])=[O:21])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C)C(=O)C.C(N(CC)CC)C>[C:9]([NH:17][C:18]1[CH:27]=[C:26](/[CH:1]=[CH:2]/[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7501Styrene2×HCID 80271Tri-o-tolylphosphineHCID 67344810HCID 67344810, compound

Product 1

HCID 57879353HCID 57879353, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalyst2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

0.83 mL of triethylamine, 34 mg of palladium acetate and 0.69 mL of styrene were added to 10 mL of N,N-dimethylacetamide solution containing 1.0 g of methyl 2-(benzamido)-1-bromobenzoate and 91 mg of tri(o-tolyl)phosphine, and stirred under nitrogen atmosphere at 120° C. for 1 hour and 30 minutes. After the reaction mixture was cooled to room temperature, 0.35 mL of styrene and 5 mg of palladium acetate were added and stirred at 120° C. for 2 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=8:1] to obtain 0.18 g of methyl 2-(benzamido)-4-((E)-2-phenylvinyl)benzoate as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringstirred at 120° C. for 2 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with a saturated sodium chloride aqueous solution
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=8:1]

Sources & evidence

ORD record
ord-cd4aa6c44a9e49428d16b49b5142b651
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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