Sodium Methoxide → HCID 18696615, compound

HRID 1870533Notes

Reaction equation

HRID 1870533 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:9]([C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:15]([O:17][CH3:18])=[O:16])[C:8](=[O:19])[N:7]([CH3:20])[N:6]=1>CO.C(COC)OC.CO>[CH3:1][O:2][C:5]1[N:9]([C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:15]([O:17][CH3:18])=[O:16])[C:8](=[O:19])[N:7]([CH3:20])[N:6]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 18696621HCID 18696621, compound

Product 1

HCID 18696615HCID 18696615, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 86595564Dimethoxyethane methanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium methoxide (16.5 mL of a 30% solution in methanol) was added to a solution of the title compound of Step C (7.9 g) in anhydrous dimethoxyethane/methanol (85 mL/35 mL). The resulting yellow solution was heated to 50° C. for 2 h under N2 and then left to stir overnight at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in methylene chloride. The resulting mixture was washed with water and then with saturated aqueous NaCl. The aqueous layer was filtered through Celite® and the filtrate was extracted three times with methylene chloride. The combined methylene chloride layers were dried (MgSO4), filtered, and concentrated under reduced pressure to give 5.4 g of an off-white solid. The crude product was purified by flash chromatography (20-100% ethyl acetate/hexane as eluent) to afford 3.9 g of the title compound of Step D as a white solid. 1H NMR (CDCl3): δ 7.58 (d,1H), 7.12 (d,1H), 3.93 (s,3H), 3.83 (s,3H), 3.44(s,3H).

Workup

  1. waitleft
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washThe resulting mixture was washed with water
  5. filtrationThe aqueous layer was filtered through Celite®
  6. extractionthe filtrate was extracted three times with methylene chloride
  7. dry with materialThe combined methylene chloride layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58fffaa5c3334f2b9d50e6ceb7172bd2
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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