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Triethylamine → HCID 44382365, compound

HRID 1059844
Notes
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Reaction equation

HRID 1059844 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent
HCID 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-10b4f92de09a41f58d247435a5ce9317
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06521658B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes