Triethylamine → HCID 44382365, compound

HRID 583933Notes

Reaction equation

HRID 583933 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]([CH3:8])[C:4](=[O:9])[CH:3]=1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([S:29](Cl)(=[O:31])=[O:30])[CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26]>O1CCOCC1.CN(C=O)C.C(OCC)(=O)C>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([S:29]([O:1][C:2]2[CH:7]=[CH:6][N:5]([CH3:8])[C:4](=[O:9])[CH:3]=2)(=[O:30])=[O:31])[CH:20]=[C:19]([O:18][CH3:17])[C:24]=1[O:25][CH3:26]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 151961583,4,5-Trimethoxybenzene-1-sulfonyl chlorideHCID 546845234-Hydroxy-1-Methyl-1h-pyridin-2-one

Product 1

HCID 44382365HCID 44382365, compoundYield 36.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-hydroxy-1-methyl-1H-pyridin-2-one ([40357-87-7], 44.9 mg, 0.358 mmol) in dioxane (2 mL) and DMF (1 mL) was treated with triethylamine (0.15 mL) and 3,4,5-trimethoxybenzenesulfonylchloride (97.1 mg, 0.358 mmol), stirred for 48 hours at room temperature, diluted with ethyl acetate, washed with 1.1M NaHSO4, dried (MgSO4), filtered and concentrated. Chromatography of the concentrate on silica gel with 40% ethyl acetate/hexane provided 47 mg of the desired compound.

Workup

  1. washwashed with 1.1M NaHSO4
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationChromatography of the concentrate on silica gel with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-bcb6abcd71154dd6bcba2e9f5c544371
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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