Acetic Acid → HCID 178509360, compound

Temperature

90 °C

3,5-Dibromo-4-cyanothiophene-2-carboxamide (5.90 g, 19.0 mmol) was suspended in dry Toluene (250 mL, 2300 mmol). 1,1-Dimethoxy-N,N-dimethylmethanamine (10.1 mL, 76.1 mmol) was added and the mixture was heated to 90° C. for 1 hour. The mixture was cooled to rt then rotavaped to dryness to give a crude intermediate. The intermediate was suspended in acetic acid (150 mL, 2600 mmol). Hydrazine hydrate (5.78 mL, 76.1 mmol) was added dropwise and the temperature was raised to 55° C. The mixture was stirred at the same temperature for 2 hours. The suspension was then evaporated to remove most of acetic acid. The resulting solid was collected by filtration and dried under vacuum to give a product (5.54 g, yield 87.2%). LCMS: (FA) ES−, 331, 333, 335. 1H NMR (300 MHz, d6-dmso) δ: 14.2 (s, br, 1H), 8.65 (s, 1H).

1. temperatureThe mixture was cooled to rt
2. customto give a crude intermediate
3. temperaturethe temperature was raised to 55° C
4. customThe suspension was then evaporated
5. customto remove most of acetic acid
6. filtrationThe resulting solid was collected by filtration
7. customdried under vacuum

ORD record

ord-3da73a4f75a54dda94d53aa0d29329df

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796271B2