Chlorosulfonyl isocyanate → HCID 86632011, compound

Temperature

-5 °C

Sulfurisocyanatidic chloride (0.752 mL, 8.63 mmol) and anhydrous nitroethane (10 mL) were mixed, cooled to −5° C. (ice/salt-bath) and a solution of 2,3-dihydro-1H-inden-5-amine (1 g, 7.51 mmol) in anhydrous nitroethane (10 mL) was added dropwise under vigorous stirring. When the addition was completed, anhydrous aluminum chloride (1.251 g, 9.39 mmol) was added and the suspension was heated at 110° C. for 60 min. The solution was cooled to room temperature and diluted with water (50 mL) and ethyl acetate (50 mL). The mixture was filtered and the layers were separated. The organic phase was dried over magnesium sulfate and concentrated under vacuum. The residue was dissolved in sulfuric acid and water (1:1 30 mL) and heated at 140° C. for 90 min before it was allowed to reach room temperature and stirred over night. The mixture was neutralized using 15% sodium hydroxide and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated under vacuum to give 0.664 g (21% yield) of the title mixture.

1. additionWhen the addition
2. temperaturethe suspension was heated at 110° C. for 60 min
3. temperatureThe solution was cooled to room temperature
4. filtrationThe mixture was filtered
5. customthe layers were separated
6. dry with materialThe organic phase was dried over magnesium sulfate
7. concentrationconcentrated under vacuum
8. dissolutionThe residue was dissolved in sulfuric acid
9. temperaturewater (1:1 30 mL) and heated at 140° C. for 90 min before it
10. customto reach room temperature
11. extractionextracted with ethyl acetate
12. dry with materialThe combined organic phases were dried over magnesium sulfate
13. concentrationconcentrated under vacuum

ORD record

ord-a83a392067b9495bb40f5148cc6a12bc

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145380B2