Potassium Carbonate → Ethyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 560677Notes

Reaction equation

HRID 560677 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[O:17])[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH:24]1([CH2:27]Br)[CH2:26][CH2:25]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH:24]1([CH2:27][N:14]2[CH2:15][CH2:16][N:12]([C:4]3[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=3)[C:13]2=[O:17])[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 57919986Ethyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

To a suspension of ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate (1.02 g, 4.00 mmol), tetra-n-butylammonium iodide (0.10 g) and potassium carbonate (0.90 g, 6.50 mmol) in acetone (80 mL) was added cyclopropylmethyl bromide (0.6 mL, 6.18 mmol). The reaction mixture was heated to reflux for 72 hours. The solvent was removed in vacuo, and the residue was washed with water (100 mL) and hexanes (30 mL) to afford the title compound in 96% yield (1.20 g): 1H NMR (300 MHz, CDCl3) δ 4.23 (q, J=7.2 Hz, 2H), 4.07 (t, J=7.8 Hz, 2H), 3.67 (t, J=7.8 Hz, 2H), 3.16 (d, J=6.9 Hz, 2H), 2.58 (s, 3H), 1.28 (t, J=7.2 Hz, 3H), 0.97-0.88 (m, 1H), 0.59-0.42 (m, 2H), 0.25-0.12 (m, 2H); MS (ES+) m/z 310.3 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 72 hours
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with water (100 mL) and hexanes (30 mL)

Sources & evidence

ORD record
ord-0d694e0f1e4747b4ae6ba6629c857a3f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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