Sodium hydride → 3,4-Dihydro-2-(3-methoxypropyl)-3-methyl-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide
Reaction equation
C([C:4]1[CH:8]=[C:7](Cl)[S:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=CC(CCO)=C[CH:15]=1)(=[O:12])=[O:11])(=O)C.[H-].[Na+].[CH3:25][O:26][CH2:27][CH2:28][CH2:29]Br>CN(C=O)C>[CH3:25][O:26][CH2:27][CH2:28][CH2:29][N:13]1[CH:14]([CH3:15])[CH2:19][C:4]2[CH:8]=[CH:7][S:6][C:5]=2[S:10]1(=[O:11])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
The product from Step B (800 mg, 3.95 mmol) was dissolved in DMF (10 mL) and the solution was cooled to -20° C. Sodium hydride (236 mg of an oil dispersion, 5.91 mmol) was added followed by 3-methoxypropyl bromide (1.8 mL, 11.82 mmol) and this mixture was warmed to 0° C. and stirred for 4 hr. The reaction mixture was poured into ice/water (50 mL) and extracted with ethyl acetate (2×100 mL). The combined extracts were washed with water (2×50 mL) and brine (2×50 mL), dried (MgSO4) and evaporated to an oil which was purified by column chromatography (silica, 10% methanol/methylene chloride) to give the desired product (890 mg, 82%).
Workup
- temperaturethis mixture was warmed to 0° C.
- extractionextracted with ethyl acetate (2×100 mL)
- washThe combined extracts were washed with water (2×50 mL) and brine (2×50 mL)
- dry with materialdried (MgSO4)
- customevaporated to an oil which
- customwas purified by column chromatography (silica, 10% methanol/methylene chloride)
Sources & evidence
- ORD record
- ord-176219f05e5c4b75b48f5425852aaacb
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05679670
Reaction notes
Loading…