Triethylamine → 5-Chloro-(3,3,3-trifluoro-1-hydroxymethyl-propyl)-thiophene-2-sulfonamide

Temperature

25 °C

To a solution of 2-amino-4,4,4-trifluoro-butan-1-ol (0.161 g, 1.12 mmol) in dry CH2Cl2 (4 mL) at 25° C. under nitrogen was added dropwise Et3N (0.17 mL, 1.23 mmol) followed also by dropwise addition of 5-chlorothiophene-2-sulfonyl chloride (0.243 g, 1.12 mmol) as a solution in dichloromethane (1 mL). The reaction was stirred for 18 h at 25° C. The reaction was then quenched by pouring it into a separatory funnel containing saturated NaHCO3 solution. Additional CH2Cl2 (15 mL) was added. After extraction, the organic layer washed with 1N HCl solution, distilled water and brine. The organic phase was then dried over MgSO4 and concentrated to a crude solid. After concentration, the crude product was purified by flash chromatography, eluent:hexane:EtOAc, 4:1 to 2:1, to obtain 5-chloro-(3,3,3-trifluoro-1-hydroxymethyl-propyl)-thiophene-2-sulfonamide as a clear oil that crystallized under vacuum (0.191 g, 53%).

1. customThe reaction was then quenched
2. additionby pouring it into a separatory funnel
3. additioncontaining saturated NaHCO3 solution
4. additionAdditional CH2Cl2 (15 mL) was added
5. extractionAfter extraction
6. washthe organic layer washed with 1N HCl solution
7. distillationdistilled water and brine
8. dry with materialThe organic phase was then dried over MgSO4
9. concentrationconcentrated to a crude solid
10. concentrationAfter concentration
11. customthe crude product was purified by flash chromatography, eluent

ORD record

ord-656e25c9d2e84402a3e46bc77dc21c4e

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547725B2