Hydrochloric Acid → HCID 15615027, compound

To a stirred, refluxing solution of N,N-dimethyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-6-carboxamide (7.57 g, 0.0314 mol) under nitrogen in tetrahydrofuran (150 ml) was added dropwise over 10 minutes borane-dimethylsulfide complex (9.4 ml, 0.094 mol). Stirring at reflux was continued for 3 hours and 6N HCl (25 ml) was added dropwise and reflux was continued for 1/2 hour. Most of the tetrahydrofuran was removed in vacuo and the residue was diluted with 6N HCl (50 ml) and was heated for 1/2 hour at steam bath temperature under nitrogen. The mixture was cooled in ice and water (100 ml) was added to dissolve the solid, washed with ether (50 ml) and basified with 10N NaOH (75 ml). The product was extracted into ethyl acetate (200 ml) in four portions, washed with water and dried over Na2SO4. The solution was filtered and concentrated in vacuo to obtain an amber oil (5.7 g). Yield was 85%.

1. additionwas added dropwise over 10 minutes borane-dimethylsulfide complex (9.4 ml, 0.094 mol)
2. temperatureat reflux
3. temperaturereflux
4. waitwas continued for 1/2 hour
5. customMost of the tetrahydrofuran was removed in vacuo
6. additionthe residue was diluted with 6N HCl (50 ml)
7. temperaturewas heated for 1/2 hour at steam bath temperature under nitrogen
8. temperatureThe mixture was cooled in ice
9. additionwater (100 ml) was added
10. dissolutionto dissolve the solid
11. washwashed with ether (50 ml)
12. extractionThe product was extracted into ethyl acetate (200 ml) in four portions
13. washwashed with water
14. dry with materialdried over Na2SO4
15. filtrationThe solution was filtered
16. concentrationconcentrated in vacuo

ORD record

ord-c42638c97ed04440bc127e95d9fa8077

Source dataset

uspto-grants-1989_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04863922