Methanol → 2-Aminothiophene-3-carboxamide

Temperature

37.5 °C

1,4-Dithiane-2,5-diol (50 g, 328 mmol), and cyanoacetamide (55.2 g, 657 mmol) were added to a mixture of MeOH (150 mL), water (9 mL) and TEA (6.5 g, 50 mmol). The resulting mixture was heated at about 35-40° C. for 30 minutes while stirring, and then heated to about 50-60° C. for an additional 30 minutes with stirring. The reaction mixture was then cooled to RT and poured into a mixture of ice (70 g)/water (200 mL). A fine precipitate formed upon addition, which was filtered and dried overnight to give (66.7 g) of the title compound. MS (ES+): 143 (M+H)+.

1. temperatureheated to about 50-60° C. for an additional 30 minutes
2. stirringwith stirring
3. temperatureThe reaction mixture was then cooled to RT
4. customA fine precipitate formed upon addition, which
5. filtrationwas filtered
6. customdried overnight

ORD record

ord-25f52f4c4edb4eb584090d5ad93df112

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745449B2