Ammonium Hydroxide → 2,4-Dibromothiazole-5-sulfonamide

To a mixture of 2,4-dibromothiazole-5-sulfonyl chloride (3.17 g, 9.28 mmol) in THF (51.4 mL) was added 33% aqueous NH4OH (24.1 mL, 278 mmol) and the reaction was stirred at room temperature for 30 minutes. The reaction was concentrated in vacuo and the residue was taken up in ethyl acetate (100 mL) and water (100 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic layers were washed with water (50 mL) and brine (50 mL), then dried and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→20/80) to give 1.7 g (57% yield) of the title compound. as a white solid. LC/MS (FA) ES+ 321, 323, 325. 1H NMR (400 MHz, DMSO-d6) δ: 8.33 (s, 2H).

1. concentrationThe reaction was concentrated in vacuo
2. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
3. washthe combined organic layers were washed with water (50 mL) and brine (50 mL)
4. customdried
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→20/80)

ORD record

ord-20aba556d99b47e0848d423042599bb1

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796271B2