Triethylamine → 3,4,5-Trimethoxyphenyl 6-methoxy-3-pyridinesulfonate

HRID 1059843Notes

Reaction equation

HRID 1059843 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][N:4]=1.C(N(CC)CC)C.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([OH:32])[CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29]>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([S:9]([O:32][C:24]2[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 695053,4,5-TrimethoxyphenolHCID 223447096-Methoxypyridine-3-sulfonyl chloride

Product 1

HCID 102868753,4,5-Trimethoxyphenyl 6-methoxy-3-pyridinesulfonateYield 83.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methoxypyridine-5-sulfonylchloride (314 mg, 1.51 mmol) in dichloromethane (15 mL) was treated with triethylamine (0.63 mL) and 3,4,5-trimethoxyphenol (279 mg, 1.51 mmol), stirred for 18 hours at room temperature, diluted with ethyl acetate, washed three times with 1M Na2CO3, dried (MgSO4), filtered, and concentrated to provide 447 mg of the desired product.

Workup

  1. washwashed three times with 1M Na2CO3
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec5884bc376d46ac9ac04bccfb85944c
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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