2-Naphthalenesulfonyl chloride → N-(6-methylpyridin-2-yl)naphthalene-2-sulfonamide

HRID 1454806Notes

Reaction equation

HRID 1454806 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][S:19]([C:10]2[CH:11]=[CH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=2)(=[O:21])=[O:20])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 157652-Amino-6-methylpyridine

Product 1

HCID 755284N-(6-methylpyridin-2-yl)naphthalene-2-sulfonamideYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-Methyl-pyridin-2-ylamine (1 g) and 2-naphthalenesulfonyl chloride (2.3 g) were dissolved in pyridine (5 mL) and the resulting mixture was allowed to stir at RT for 12 hours. After concentration in vacuo the residue was taken up in EtOAc, the solution washed with 1 N aqueous HCl, saturated brine then dried over sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography (heptane/EtOAc 5:1) to give the desired product naphthalene-2-sulfonic acid (6-methyl-pyridin-2-yl)-amide as a white foam (2.18 g). MS (ESI−): 297.2 ([M−H]−).

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. washthe solution washed with 1 N aqueous HCl, saturated brine
  3. dry with materialthen dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (heptane/EtOAc 5:1)

Sources & evidence

ORD record
ord-1cbdb46f046b405ab88029d9f230c241
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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