Potassium Carbonate → Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylate

HRID 2067348Notes

Reaction equation

HRID 2067348 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].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][N:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]2=[O:17])[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 57919776Ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate

Product 1

HCID 58031446Ethyl 4-methyl-2-(2-oxo-3-phenylimidazolidin-1-yl)thiazole-5-carboxylateYield 89%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a degassed solution of ethyl 4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxylate (1.28 g, 5.00 mmol), iodobenzene (0.70 mL, 6.15 mmol), potassium carbonate (0.83 g, 6.00 mmol) and rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.08 mL, 0.50 mmol) in dioxane (50 mL) was added copper(I) iodide (0.10 g, 0.50 mmol). The reaction mixture was heated to reflux for 16 hours. The solvent was removed in vacuo, and the residue was suspended in water and filtered. The solid was collected and washed with water (200 mL) and t-butyl methyl ether (100 mL) to afford the title compound in 89% yield (1.49 g): 1H NMR (300 MHz, DMSO-d6) δ 7.69-7.08 (m, 5H), 4.28-4.13 (m, 6H), 2.62 (s, 3H), 1.30 (t, J=6.9 Hz, 3H); MS (ES+) m/z 332.4 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. filtrationfiltered
  5. customThe solid was collected
  6. washwashed with water (200 mL) and t-butyl methyl ether (100 mL)

Sources & evidence

ORD record
ord-98af75df389042a08b7fd90184d18efe
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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