HCID 67945849, compound → HCID 67945766, compound

To a stirring, refluxing solution of N,N-dimethyl-4-oxo-5,6-dihydro-4H-furano[2,3-b]thiopyran-6-carboxamide (7.1 g, 0.0314 mol) in tetrahydrofuran (150 ml) was added dropwise borane-dimethyl sulfide complex (9.4 ml, 0.014 mol). The reaction was then stirred at reflux for 3 hr. when 6NHCl (25 ml) was added slowly and the reaction was heated at reflux for a further 1/2 hr. Most of the tetrahydrofuran was removed in vacuo and the residue was diluted with 6N HCl (50 ml) and heated again for 1/2 hr. The reaction was cooled to room temperature and water (100 ml) was added. The reaction was extracted once with ether (50 ml) and then basified with 10N NaOH (75 ml). The product was extracted with ethyl acetate (4×50 ml portions). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the product.

1. additionwas added dropwise borane-dimethyl sulfide complex (9.4 ml, 0.014 mol)
2. temperatureat reflux for 3 hr
3. additionwhen 6NHCl (25 ml) was added slowly
4. temperaturethe reaction was heated
5. temperatureat reflux for a further 1/2 hr
6. customMost of the tetrahydrofuran was removed in vacuo
7. additionthe residue was diluted with 6N HCl (50 ml)
8. temperatureheated again for 1/2 hr
9. additionwater (100 ml) was added
10. extractionThe reaction was extracted once with ether (50 ml)
11. extractionThe product was extracted with ethyl acetate (4×50 ml portions)
12. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customto give the product

ORD record

ord-bfc69e4f29054474881a72a781450adf

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05045561