Sodium hydride → 3,4-Dihydro-2-(3-methoxypropyl)-3-methyl-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide
Reaction equation
[CH3:1][CH:2]1[CH2:7][C:6]2[CH:8]=[CH:9][S:10][C:5]=2[S:4](=[O:12])(=[O:11])[NH:3]1.[H-].[Na+].[CH3:15][O:16][CH2:17][CH2:18][CH2:19]Br>CN(C=O)C>[CH3:15][O:16][CH2:17][CH2:18][CH2:19][N:3]1[CH:2]([CH3:1])[CH2:7][C:6]2[CH:8]=[CH:9][S:10][C:5]=2[S:4]1(=[O:12])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
The product from Step B (800 mg, 3.94 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-548253e241e04e7797f7dc2667842ca8
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05378703
Reaction notes
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