Sodium Acetate → 5-Benzyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-(4-methoxy-phenyl)-thiazole

HRID 556116Notes

Reaction equation

HRID 556116 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH2:15])=[S:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH:17]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=O.C([O-])(=O)C.[Na+]>C(O)C>[CH2:28]([C:17]1[S:14][C:13]([CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:15][C:18]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 137372192-Bromo-1-(4-methoxyphenyl)-3-phenylpropan-1-oneHCID 536396423-(3,4-Dimethoxy-phenyl)-thiopropanamide

Product 1

HCID 579916295-Benzyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-(4-methoxy-phenyl)-thiazoleYield 71.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 50 ml eggplant-shaped bottle were added 0.12 g (0.533 mmol) 3-(3,4-dimethoxy-phenyl)-thiopropanamide prepared in the step 3, 0.17 g (0.533 mmol) 2-bromo-1-(4-methoxy-phenyl)-3-phenyl-propan-1-one prepared in the step 3 of Example 1, 0.04 g (0.533 mmol) anhydrous sodium acetate and 20 ml anhydrous ethanol. The resulting mixture was refluxed for 4 hours, when TLC showed the completion of the reaction, and concentrated under a reduced pressure. The reaction mixture was partitioned between water and ethyl acetate each 20 ml, the ethyl acetate layer was washed with saturated brine 2×10 ml, dried over anhydrous Na2SO4, filtered and concentrated to give a solid crude product which was recrystallized with petroleum ether and ethyl acetate to obtain a 0.17 g product as a thick liquid in a yield of 70.8%. 1H-NMR (CDCl3, 400 MHz) δ: 3.06 (2H, t, J=8.40 Hz, CH2), 3.25 (2H, t, J=8.40 Hz, CH2), 3.83 (3H, s, CH3O), 3.84 (3H, s, CH3O), 3.86 (3H, s, CH3O), 4.20 (2H, s, CH2), 6.70˜6.80 (3H, m, ArH), 6.95 (2H, d, J=8.80 Hz, ArH), 7.15˜7.35 (5H, m, ArH), 7.54 (2H, d, J=8.80 Hz, ArH); EI-MS m/e (%): 445.1 (M, 100), 151.1 (93); HREI-MS Calcd. for C27H27NO3S: 445.1712. found: 445.1716.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. customthe completion of the reaction
  3. concentrationconcentrated under a reduced pressure
  4. customThe reaction mixture was partitioned between water and ethyl acetate each 20 ml
  5. washthe ethyl acetate layer was washed with saturated brine 2×10 ml
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a solid crude product which
  10. customwas recrystallized with petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-74d0980514ef46a9845d2185b62dd93b
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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