Potassium Carbonate → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-one

HRID 1882446Notes

Reaction equation

HRID 1882446 reaction equation
[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[O:14])=[N:6][C:5]=1[CH3:15])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH:22]1([CH2:25][CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:24][CH2:23]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:26][CH2:25][CH:22]3[CH2:24][CH2:23]3)[C:10]2=[O:14])=[N:6][C:5]=1[CH3:15])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterHCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-one

Product 1

HCID 666615211-(5-Acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-oneYield 37%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one (4.50 g, 20.00 mmol), tetrabutylammonium iodide (0.10 g) and potassium carbonate (4.00 g, 28.92 mmol) in 1,4-dioxane (100 mL) was added 2-cyclopropylethyl-4-methylbenzenesulfonate (6.00 g, 24.96 mmol). The reaction mixture was heated to reflux for 37 h. The solvent was removed in vacuo. The residue was dissolved in water (50 mL) and extracted with ethyl acetate. The organic solution washed with water and brine and dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography to afford 1-(5-acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl)imidazolidin-2-one in 37% yield (2.20 g): mp 82-83° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 4.12-4.06 (m, 2H), 3.63-3.57 (m, 2H), 3.40 (t, J=7.2 Hz, 2H), 2.60 (s, 3H), 2.44 (s, 3H), 1.51-1.44 (m, 2H), 0.71-0.62 (m, 1H), 0.49-0.43 (m, 2H), 0.09-0.04 (m, 2H); MS (ES+) m/z 294.2 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 37 h
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in water (50 mL)
  5. extractionextracted with ethyl acetate
  6. washThe organic solution washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6e17f98731eb47a486bc1fffc799991f
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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