Trichloromethanethiol → HCID 21928608, compound

Temperature

-10 °C

A mixture of isonicotinimidamide hydrochloride (1.0 g, 6.35 mmol) and NEt3 (3.21 g, 4.42 mL, 31.7 mmol) in 50 mL DCM was cooled to −5 and −10° C. Perchloromethyl mercaptan (1.3 g, 763 μl, 6.98 mmol) in 10 mL DCM was added drop wise over 1 h. The mixture was warmed to 0° C. over 30 min and stirred for 2 h. Water (50 mL) and 2M NaOH (10 mL) was added. The suspension was filtrated. The organic layer was extracted with DCM and washed with brine (50 mL) and the aqueous layer was extracted with DCM (50 mL). The organic layers were combined, dried over Na2SO4 and filtered off. The crude product was concentrated under vacuum and the residue dissolved in DCM, taken up on Isolute® and purified by column chromatography on silica eluting with a gradient formed from heptane and EtOAc to yield after evaporation of the product containing fraction 0.43 g (34%) of the title compound as a brown solid. MS (m/e): 198.1 (MH+).

1. temperatureThe mixture was warmed to 0° C. over 30 min
2. filtrationThe suspension was filtrated
3. extractionThe organic layer was extracted with DCM
4. washwashed with brine (50 mL)
5. extractionthe aqueous layer was extracted with DCM (50 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered off
8. concentrationThe crude product was concentrated under vacuum
9. dissolutionthe residue dissolved in DCM
10. custompurified by column chromatography on silica eluting with a gradient
11. customformed from heptane and EtOAc
12. customto yield
13. customafter evaporation of the product
14. additioncontaining fraction 0.43 g (34%) of the title compound as a brown solid

ORD record

ord-238f04eac56c4fbf910a2026fb96bb3f

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09023852B2