Methanol → HCID 19026998, compound

Temperature

70 °C

A suspension of 4-acetamido-3,4-dihydro-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (4.93 g, 0.02 mol) in tetrahydrofuran (50 ml) was heated in an oil bath at 70° C. Borane-dimethyl sulfide complex (20.0 ml of 10.0M, 0.20 mol) was added dropwise over 1/2 hour and the mixture was stirred at 70° C. for 4 hrs. The mixture was cooled in ice and methanol was added (50 ml) dropwise. The volatile solvents were removed in vacuo and the residual oil was heated with 6N hydrochloric acid (50 ml) on the steam bath for 1/2 hr. Ethyl acetate (200 ml) was added and the mixture was basified with sodium bicarbonate. Methanol (20 ml), was added, the mixture filtered and the aqueous layer was re-extracted with ethyl acetate (100 ml) -methanol (10 ml). The organic solutions were combined, dried and concentrated in vacuo. A colorless viscous oil (4.47 g) was recovered. Yield 96%.

1. additionBorane-dimethyl sulfide complex (20.0 ml of 10.0M, 0.20 mol) was added dropwise over 1/2 hour
2. temperatureThe mixture was cooled in ice
3. customThe volatile solvents were removed in vacuo
4. temperaturethe residual oil was heated with 6N hydrochloric acid (50 ml) on the steam bath for 1/2 hr
5. additionEthyl acetate (200 ml) was added
6. additionMethanol (20 ml), was added
7. filtrationthe mixture filtered
8. extractionthe aqueous layer was re-extracted with ethyl acetate (100 ml) -methanol (10 ml)
9. customdried
10. concentrationconcentrated in vacuo
11. customA colorless viscous oil (4.47 g) was recovered

ORD record

ord-f247a9605cf3443e9d0d33a8773b65be

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05308842