Aluminum(III) Chloride → HCID 18931442, compound

HRID 1598973Notes

Reaction equation

HRID 1598973 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)[C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)C(Cl)Cl>[CH3:12][C:11]1([CH3:13])[C:20]2[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:9](=[O:14])[CH2:10]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 18931461HCID 18931461, compound2×

Product 1

HCID 18931442HCID 18931442, compoundYield 7.5%

Reagents, catalysts & solvents 1

HCID 65741,1,2-TrichloroethaneSolvent

Procedure

To a solution of 55 mg (0.19 mmol) of N-(4-methylphenyl)-N-(3-methoxyphenyl)-3,3-dimethylacrylamide (Compound 16) in 2.0 mL of trichloroethane stirring under argon, was added 0.11 g (0.84 mmol) of aluminum chloride and the mixture was heated at 90°-100° C. for 18 hours. The reaction was cooled, poured onto ice, the mixture extracted with diethyl ether (2x) dried (MgSO4), filtered and concentrated in vacuo to give an oil. The mixture was purified by flash chromatography (30% ethyl acetate in hexanes) to give the title compound as a white solid (4.0 mg). PNMR (300 MHz, CDCl3) d 1.37 (6 H, s), 2.41 (3 H, s), 2.65 (2 H, s), 4.76 (1 H, s), 5.92 (1 H, d, J=2.6 Hz), 6.49 (1 H, rid, J=8.3, 2.6 Hz), 7.09 (2 H, d, J=8.1 Hz), 7.17 (1 H, d, J=8.3 Hz), 7.30 (2 H, d, J=8.1 Hz).

Workup

  1. temperaturethe mixture was heated at 90°-100° C. for 18 hours
  2. temperatureThe reaction was cooled
  3. additionpoured onto ice
  4. extractionthe mixture extracted with diethyl ether (2x)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an oil
  9. customThe mixture was purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-02b59c45a0d4475684a08d076a5bdd9b
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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