Ammonia → 3,5-Dibromo-4-cyanothiophene-2-carboxamide

3,5-Dibromo-4-cyanothiophene-2-carboxylic acid (5.90 g, 18.6 mmol) was added to a solution of thionyl chloride (27.1 mL, 371 mmol) in acetonitrile (40.0 mL, 766 mmol). The mixture was refluxed for 30 min then cooled to rt. The solvent was evaporated in vacuo to dryness to yield a lightly yellow solid. Methylene chloride (100 mL, 2000 mmol) was added to dissolve the solid, then the solution was cooled to 0° C. Under a nitrogen atmosphere, a solution of 0.500 M ammonia in 1,4-dioxane (111.5 mL, 55.7 mmol) was slowly added, and the mixture was brought to room temperature for 1 h. The mixture was evaporated in vacuo to give a solid residue. 100 mL of 1N HCl was added and the suspension was stirred for 1 h at room temperature. The solid product was collected by filtration and dried under high vacuum to give product (5.64 g, yield 98%). LCMS: (FA) ES−, 308, 310, 312.

1. temperatureThe mixture was refluxed for 30 min
2. customThe solvent was evaporated in vacuo to dryness
3. customto yield a lightly yellow solid
4. dissolutionto dissolve the solid
5. temperaturethe solution was cooled to 0° C
6. customThe mixture was evaporated in vacuo
7. customto give a solid residue
8. filtrationThe solid product was collected by filtration
9. customdried under high vacuum

ORD record

ord-a5428f12643e4861b7fa53dd339072e9

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796268B2