Acetonitrile → [1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetic acid methyl ester

温度

55 °C

To a solution of the product from Step B (8.00 g, 20.9 mmol) in acetonitrile (70 mL) was added 4-cyanobenzyl bromide (4.10 g, 20.92 mmol) and heated at 55° C. for 3 hours. The reaction was cooled to room temperature and the resulting imidazolium salt was collected by filtration. The filtrate was heated at 55° C. for 18 hours. The reaction mixture was cooled to room temperature and evaporated in vacuo. To the residue was added EtOAc (70 mL) and the resulting precipitate collected by filtration. The precipitated imidazolium salts were combined, suspended in methanol (100 mL) and heated to reflux for 30 minutes. After this time, the solvent was removed in vacuo. The resulting residue was suspended in EtOAc (75 mL) and the solid isolated by filtration and washed with EtOAc. The solid was treated with sat. aq. NaHCO3 solution (300 mL) and CH2Cl2 (300 mL) and stirred at room temperature for 2 hours. The organic layer was separated, dried, (MgSO4) and evaporated in vacuo to afford the title compound as a white solid.

1. temperatureThe reaction was cooled to room temperature
2. filtrationthe resulting imidazolium salt was collected by filtration
3. temperatureThe filtrate was heated at 55° C. for 18 hours
4. temperatureThe reaction mixture was cooled to room temperature
5. customevaporated in vacuo
6. additionTo the residue was added EtOAc (70 mL)
7. filtrationthe resulting precipitate collected by filtration
8. temperatureheated
9. temperatureto reflux for 30 minutes
10. customAfter this time, the solvent was removed in vacuo
11. customthe solid isolated by filtration
12. washwashed with EtOAc
13. additionThe solid was treated with sat. aq. NaHCO3 solution (300 mL) and CH2Cl2 (300 mL)
14. customThe organic layer was separated
15. customdried
16. custom(MgSO4) and evaporated in vacuo

ORDレコード

ord-66a6c651181340e999bb461e5151c884

出典データセット

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05859035