3,4-Dimethoxyaniline → HCID 43388282, compound

HRID 1772901Notes

Reaction equation

HRID 1772901 reaction equation
[Cl:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[NH2:17]>O1CCOCC1>[Cl:1][C:2]1[C:7]([S:8]([NH:17][C:16]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:14]([O:13][CH3:12])[CH:15]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 227703,4-DimethoxyanilineHCID 102199682-Chloropyridine-3-sulfonyl chloride

Product 1

HCID 43388282HCID 43388282, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloropyridine-3-sulfonyl chloride (500 mg, 2.36 mmol) and 3,4-dimethoxyaniline (397 mg, 2.59 mmol) in 1,4-dioxane (10 mL) was stirred for 1 h at 0° C. The reaction mixture was filtered, the residue washed with ether and the filtrate concentrated in vacuo. Purification by gradient column chromatography eluting with 10-60% EtOAc in iso-hexane yielded the title compound (352 mg, 1.07 mmol).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with ether
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by gradient column chromatography
  5. washeluting with 10-60% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-1bde3906db9e4790a3defb748c0f5dff
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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