Trichloroacetyl isocyanate → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-, carbamate (ester)

Temperature

-30 °C

In 15 ml of dry tetrahydrofuran was dissolved 1.5 g (4.2 mmol) of the alcohol compound (123a), and the mixture was cooled to -30° C., followed by addition of 1.2 g (6.4 mmol) of trichloroacetylisocyanate. After 5 minutes, the mixture was warmed to 0° C., and stirred for 10 minutes. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water, and ethyl acetate was distilled off. To the residue was added 15 ml of methanol, 0.26 g of triethylamine and 0.72 ml of water, and the mixture was heated at 50° C. for 0.5 hours. The mixture was diluted with ice-water, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (2% methanol:ethyl acetate), and recrystallized from ethyl acetate-n-hexane to give 1.5 g of Compound I-137 as crystals (yield 89%). mp 161-162° C.

1. temperaturethe mixture was warmed to 0° C.
2. extractionextracted with ethyl acetate
3. washThe extract was washed with water, and ethyl acetate
4. distillationwas distilled off
5. additionTo the residue was added 15 ml of methanol, 0.26 g of triethylamine and 0.72 ml of water
6. temperaturethe mixture was heated at 50° C. for 0.5 hours
7. additionThe mixture was diluted with ice-water
8. extractionextracted with ethyl acetate
9. washThe extract was washed with water
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (2% methanol:ethyl acetate)
14. customrecrystallized from ethyl acetate-n-hexane

ORD record

ord-d9308f50459f457c997e7c64e88a69df

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06147097