Potassium Carbonate → Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate
Reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5](=[O:18])[NH:6][C:7]1[S:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:17])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:17][C:9]1[CH:8]=[C:7]([N:6]2[CH2:2][CH2:3][NH:4][C:5]2=[O:18])[S:11][C:10]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]Participants
Conditions
- Temperature
- 70 °C
Procedure
A mixture of ethyl 5-(3-(2-chloroethyl)ureido)-3-methylthiophene-2-carboxylate (6.11 g, 21.02 mmol) and potassium carbonate (2.91 g, 21.0 mmol) in anhydrous acetonitrile (60 mL) was stirred under nitrogen atmosphere at 70° C. for 5 h, and then was allowed to cool to ambient temperature and was partitioned between ethyl acetate (200 mL) and water (100 mL). The aqueous layer was extracted with 10% methanol in dichloromethane (2×100 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with 20% ethyl acetate in hexanes to afford the title compound as a cream solid in 88% yield (4.70 g): 1H NMR (300 MHz, CDCl3) δ 6.16 (s, 1H), 5.15 (br s, 1H), 4.28 (q, J=7.1 Hz, 2H), 3.97-3.89 (m, 2H), 3.71-3.64 (m, 2H), 2.50 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 255.2 (M+1).
Workup
- temperatureto cool to ambient temperature
- customwas partitioned between ethyl acetate (200 mL) and water (100 mL)
- extractionThe aqueous layer was extracted with 10% methanol in dichloromethane (2×100 mL)
- dry with materialThe combined organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was triturated with 20% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-2e9e6f1d28314492b04121f3aaa3fb00
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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