Triethylamine → HCID 90418265, compound

Temperature

0 °C

Into a 50-mL round-bottom flask, was placed [3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol (80 mg, 0.27 mmol, 1.00 equiv), dichloromethane (2.0 mL), triethylamine (83 mg, 0.82 mmol, 3.01 equiv). This was followed by the addition of MsCl (62 mg, 0.54 mmol, 2.00 equiv) dropwise with stirring at 0° C. The resulting solution was stirred for 1 h at 30° C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×10 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.12 g of [3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methyl methanesulfonate as a yellow solid. This crude could be used for the next step directly. Mass spectrum (ESI, m/z): Calcd. for C12H9ClF3NO3S2, 372.0 (M+H). found 372.0.

1. customInto a 50-mL round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 1 h at 30° C
3. customThe reaction was then quenched by the addition of 10 mL of water
4. extractionThe resulting solution was extracted with 3×10 mL of dichloromethane
5. washThe resulting mixture was washed with 2×20 mL of sodium chloride
6. dry with materialThe mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum
8. customThis resulted in 0.12 g of [3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methyl methanesulfonate as a yellow solid

ORD record

ord-e9d9c5d88db244659408daf493c2f87e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1