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

HRID 554929Notes

Reaction equation

HRID 554929 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]Br)[CH2:24][CH2:23]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([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 81503BromomethylcyclopropaneHCID 579197381-(5-Acetyl-4-methylthiazol-2-yl)imidazolidin-2-one

Product 1

HCID 579197631-(5-Acetyl-4-methylthiazol-2-yl)-3-(cyclopropylmethyl)imidazolidin-2-oneYield 33%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)imidazolidin-2-one (2.25 g, 10.00 mmol), tetrabutylammonium iodide (0.10 g) and potassium carbonate (3.50 g, 25.27 mmol) in tetrahydrofuran (100 mL) was added cyclopropylmethyl bromide (2.0 mL, 20.88 mmol). The reaction mixture was heated to reflux for 50 hours. The solvent was removed in vacuo, and the residue was washed with water and hexanes to afford the title compound in 33% yield (0.94 g): mp 103-104° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 4.14-4.05 (m, 2H), 3.72-3.69 (m, 2H), 3.19 (d, J=6.0 Hz, 2H), 2.57 (s, 3H), 2.44 (s, 3H), 0.99-0.89 (m, 1H), 0.59-0.55 (m, 2H), 0.27-0.22 (m, 2H); MS (ES+) m/z 280.2 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 50 hours
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with water and hexanes

Sources & evidence

ORD record
ord-e573ff120c1d49638b5db0234b518ae1
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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