1,1'-Carbonyldiimidazole → HCID 178505356, compound

5-(4-chlorophenyl)furan-2-carboxylic acid (208 mg, 0.93 mmol) was dissolved in THF (5 ml), to which 1,1′-carbonyldiimidazole (CDI) (182 mg, 1.12 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. 2 M guanidine solution (2.73 ml, 5.45 mmol) prepared in Example 1 was added thereto, and the mixture was reacted at room temperature for 12 hours. After completion of the reaction, the solution was added with saturated brine (20 ml) and extracted with ethyl acetate (30 ml×3). The organic layer was washed with 10% brine, dried over anhydrous magnesium sulfate (MgSO4), and concentrated in vacuo. The residue was dissolved in acetone (4 ml), to which methanesulfonic acid (0.2 ml) was added and then cooled down to 0° C. to precipitate solid. The precipitated solid was collected by filtration to give 234 mg of a title compound (yield: 70%).

1. additionwas added
2. customthe mixture was reacted at room temperature for 12 hours
3. customAfter completion of the reaction
4. extractionextracted with ethyl acetate (30 ml×3)
5. washThe organic layer was washed with 10% brine
6. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
7. concentrationconcentrated in vacuo
8. dissolutionThe residue was dissolved in acetone (4 ml), to which methanesulfonic acid (0.2 ml)
9. additionwas added
10. temperaturecooled down to 0° C.
11. customto precipitate solid
12. filtrationThe precipitated solid was collected by filtration

ORD record

ord-042427d2f23f4da49b04cd65e9a4fecb

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07351843B2