Cyanoacetamide → 2-Aminothiophene-3-carboxamide

Triethylamine (36 mL, 256 mmol) was added to the solution of 2-cyanoacetamide (10.8 g, 128 mmol) and [1,4]-dithiane-2,5-diol (19.5 g, 128 mmol) in ethanol (400 mL). The resulting reaction mixture was stirred at room temperature for 5 min, then heated at reflux for 2 h. After the reaction mixture is cooled to room temperature, it was filtered and concentrated under vacuum. The residue was then taken up into ethyl acetate (400 mL) and washed with aqueous sodium hydroxide (1 M, 1×200 mL), water (2×200 mL) and brine (1×200 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give the above titled compound as a light yellow solid (16 g, 113 mmol, 88% yield). LC-MS [M+H]+ m/z 143.

1. customThe resulting reaction mixture
2. temperatureheated
3. temperatureat reflux for 2 h
4. temperatureAfter the reaction mixture is cooled to room temperature
5. filtrationit was filtered
6. concentrationconcentrated under vacuum
7. washwashed with aqueous sodium hydroxide (1 M, 1×200 mL), water (2×200 mL) and brine (1×200 mL)
8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
9. concentrationconcentrated under vacuum

ORD record

ord-c1e29f2b2b8e41fe83a2229d03159c09

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375131B2