Sodium hydride → HCID 22901897, compound

HRID 1489816Notes

Reaction equation

HRID 1489816 reaction equation
[OH:1][CH:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[S:5](=[O:12])(=[O:11])[NH:4][CH2:3]1.[H-].[Na+].[CH3:15][O:16][CH2:17][CH2:18][CH2:19]Br>CN(C=O)C>[OH:1][CH:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[S:5](=[O:12])(=[O:11])[N:4]([CH2:19][CH2:18][CH2:17][O:16][CH3:15])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5245511-Bromo-3-methoxypropaneHCID 229019424-Hydroxy-3,4-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1(2H)-dione

Product 1

HCID 22901897HCID 22901897, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. customthen quenched with water (200 mL)
  2. extractionextracted with ethyl acetate (4×30 mL)
  3. washwashed with water (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure which
  6. customprovided an oil which
  7. customwas purified by column chromatography (silica, gradient: hexane to ethyl acetate)

Sources & evidence

ORD record
ord-88aa6f12fda945dd82f6513ea9e70b86
Source dataset
uspto-grants-1997_10
Patent number
US05679670

Reaction notes

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