3-Thiophencarboxamide,N-methyl- → HCID 10244631, compound

Temperature

20 °C

To suspension of N-methyl-3-thiophenecarboxamide (1.12 g) (prepared according to J. Org. Chem. (1976), 41(23), 3668-74) in concentrated aqueous sulphuric acid (25 ml) at 0-5° C. was added N-(hydroxymethyl)trifluoroacetamide (1.134 g). The suspension was allowed to warm to 20° C. and stirred for 2 h. The mixture was poured onto ice (150 g) and diluted with ethyl acetate (200 ml). The biphase mixture was diluted with saturated sodium hydrogen carbonate (200 ml) and treated with sodium hydrogen carbonate (21 g). The phases were separated and the organic phase washed with saturated sodium hydrogen carbonate (150 ml×2). The combined aqueous phases were extracted with ethyl acetate (100 ml). The combined organic extracts were concentrated in vacuo. The residue was pre-absorbed onto silica and purified by biotage (90 g) eluting with 1:1 to 0:1 cyclohexane:ethyl acetate to give the title compound as a white solid (0.7129).

1. additionThe mixture was poured onto ice (150 g)
2. customThe phases were separated
3. washthe organic phase washed with saturated sodium hydrogen carbonate (150 ml×2)
4. extractionThe combined aqueous phases were extracted with ethyl acetate (100 ml)
5. concentrationThe combined organic extracts were concentrated in vacuo
6. customThe residue was pre-absorbed onto silica
7. custompurified by biotage (90 g)
8. washeluting with 1:1 to 0:1 cyclohexane

ORD record

ord-be5173694d8d4c139d62c84e87399bc1

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622464B2