Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-Bromo-3-methoxypropane | HCID 524551 | — |
| Reactant | 4-Hydroxy-3,4-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1(2H)-dione | HCID 22901942 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22901897 | HCID 22901897 | 63% |
Reaction Steps
The product from Example 1, Step C (2.0 g, 9.74 mmol) was added to a suspension of sodium hydride (0.4 g, 10.0 mmol, of a 60% suspension in mineral oil) in DMF (30 ML) and the mixture was stirred for 1hr. then cooled to 0° C. 3-Bromopropyl methyl ether (1.5 g, 9.74 mmol) was added and the mixture was stirred overnight then quenched with water (200 mL), and extracted with ethyl acetate (4×30 mL). The extracts were combined, washed with water (100 mL), dried (MgSO4) and concentrated under reduced pressure which provided an oil which was purified by column chromatography (silica, gradient: hexane to ethyl acetate) to give 1.7 g (63%) of a clear oil which was not purified further.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05679670 |
|---|
| Source dataset | uspto-grants-1997_10 |
|---|
| ORD ID | ord-88aa6f12fda945dd82f6513ea9e70b86 |
|---|
| Source note | uspto-grants-1997_10 |
|---|