Triethylamine → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((4-nitrophenyl)methyl)-, carbamate (ester)

Temperatur

-20 °C

In 5 ml of tetrahydrofuran was dissolved 467 mg (1 mmol) of 5-(3,5-dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl-1-p-nitrobenzyl-1H-imidazole (126a), and there was added 0.23 g (1.2 mmol)of trichloroacetylisocyanate under stirring on a cooling bath at -20° C. Then, the bath was taken off, and the mixture was reacted for 2 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and extracted with methylene chloride. The extract was washed with water, dried, and the solvent was distilled off, and the trichloroacetylcarbamoyloxy compound which was able to use for the next reaction, was obtained in the residue. The intermediate was dissolved in 10 ml of aqueous methanol (10%), followed by addition of 0.2 ml of triethylamine under stirring at room temperature, and the mixture was stirred with heating at 50° C. for 3 hours and worked up. When the crystals were precipitated, the mixture was filtered directly. When the crystals were not precipitated, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and extracted with methylene chloride. The extract was washed with water and dried, the solvent was distilled off, and the residue was purified by silica gel column chromatography (ethyl acetate) to give 2-(2-carbamoyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(p-nitrobenzyl)-1H-imidazole (128a)as oil (yield 98%)

1. customthe mixture was reacted for 2 hours
2. extractionextracted with methylene chloride
3. washThe extract was washed with water
4. customdried
5. distillationthe solvent was distilled off
6. customto use for the next reaction
7. customwas obtained in the residue
8. stirringunder stirring at room temperature
9. stirringthe mixture was stirred
10. temperaturewith heating at 50° C. for 3 hours
11. customWhen the crystals were precipitated
12. filtrationthe mixture was filtered directly
13. customWhen the crystals were not precipitated
14. additiona saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture
15. extractionextracted with methylene chloride
16. washThe extract was washed with water
17. customdried
18. distillationthe solvent was distilled off
19. customthe residue was purified by silica gel column chromatography (ethyl acetate)

ORD-Eintrag

ord-69137dfad3cd477480651d454a0fe178

Quelldatensatz

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05910506