Water → HCID 14047059, compound

HRID 77689Notes

Reaction equation

HRID 77689 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH3:21][NH2:22].O>CN(C)C=O>[CH3:19][C:16]1[CH:15]=[CH:14][C:13]([CH:12]2[CH2:11][C:10](=[O:20])[CH2:9][CH:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)[N:22]2[CH3:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 2630611,5-Bis(4-methylphenyl)-1,4-pentadien-3-one

Product 1

HCID 14047059HCID 14047059, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,5-Bis(4-methylphenyl)-1,4-pentadien-3-one (20aa, 0.32 g, 1.2 mmol) was dissolved in dimethyl formamide (9 ml). Methylamine (51, 0.5 ml, 5.8 mmol, 40% in water) was added and the mixture stirred for 72 hr at room temperature. The mixture was poured into water (50 ml) and stirred for 2 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to afford a solid that was recrystallized from ethanol to give 0.26 g (75%) of a white solid: mp 120-121° C. [expected mp 105-107° C.]; 1H NMR δ 1.79 (s, 3H), 2.36 (s, 6H), 3.10 (d, 2H, J=14.9 Hz), 2.79 (t, 2H, J=13.1 Hz), 3.35 (dd, 2H, J=11.9, 2.4 Hz), 7.15 (d, 4H, J=8.0 Hz), 7.21 (d, 4H, J=7.9 Hz); 13C NMR: δ 21.2, 40.7, 50.9, 70.0, 126.9, 129.4 137.2, 140.2, 207.1.

Workup

  1. stirringstirred for 2 hr at room temperature
  2. extractionThe resulting mixture was extracted into ethyl acetate
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford a solid
  8. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
  9. customto afford a solid
  10. customthat was recrystallized from ethanol

Sources & evidence

ORD record
ord-e39dc54aa1de41b98623f165a46c92e1
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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