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

HRID 583932

Reaction equation

HRID 583932 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-e5cf63a01e114696b9636a9a1471802b
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Linked notes

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