Dimethyl Sulfoxide → 5,7-Dibromo-6-methoxy-1,3-benzothiazol-2-amine

Temperature

90 °C

Anhydrous DMSO (2 mL) was added to a mixture of ethyl N-[(2,3,5-tribromo-4-methoxy-phenyl)carbamothioyl]carbamate (426 mg, 1.02 mmol), CuO (8 mg, 0.10 mmol) and potassium carbonate (211 mg, 1.53 mmol). The mixture was sonicated then heated to 90° C. in a pre-heated heating block under air. The mixture was cooled to rt after 55 minutes and diluted with water. The mixture was extracted into EtOAc (3×50 mL) and the combined organic layers were washed with water then brine. The organic layer was dried over Na2SO4 and the mixture filtered through a PTFE filter to remove copper salts, then the filtrate was concentrated to dryness under reduced pressure. The desired compound was obtained as an off-white solid, 208 mg (60% over 2 steps). m/z: 337.01/339.01/340.97 [M+H]+.

1. customThe mixture was sonicated
2. temperatureheating block under air
3. temperatureThe mixture was cooled to rt after 55 minutes
4. extractionThe mixture was extracted into EtOAc (3×50 mL)
5. washthe combined organic layers were washed with water
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationthe mixture filtered through a PTFE
8. filtrationfilter
9. customto remove copper salts
10. concentrationthe filtrate was concentrated to dryness under reduced pressure

ORD record

ord-133a24d132a84b4f8f3e07e74710c379

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181234B2