HCID 22484945, compound → HCID 14912438, compound

Temperature

50 °C

(E)-N-tert-Butyl-2-(4-pyridyl)ethenesulfonamide (3.8 g) was dissolved in trifluoroacetic acid (38 ml) and the mixture was stirred in an oil bath at 50° C. for 4 hr. The reaction mixture was concentrated to dryness under reduced pressure. The residue was dissolved in trifluoroacetic acid (19 ml) and stirred in an oil bath at 50° C. for 45 min. The reaction mixture was concentrated to dryness under reduced pressure and the residue was partitioned between chloroform:methanol (9:1) and a saturated aqueous solution of sodium hydrogen carbonate. The aqueous layer was extracted twice with chloroform:methanol (9:1) and once with ethyl acetate. The aqueous layer was saturated with sodium chloride and extracted 4 times with ethyl acetate. All extracts with ethyl acetate were combined, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was powdered from diethyl ether to give (E)-2-(4-pyridyl)ethenesulfonamide (2.34 g) as a pale-brown powder.

1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
2. dissolutionThe residue was dissolved in trifluoroacetic acid (19 ml)
3. stirringstirred in an oil bath at 50° C. for 45 min
4. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
5. customthe residue was partitioned between chloroform:methanol (9:1)
6. extractionThe aqueous layer was extracted twice with chloroform:methanol (9:1) and once with ethyl acetate
7. extractionextracted 4 times with ethyl acetate
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-76ba65ec9372441195c93f3d1cc7ea17

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06573274B1