Pyridine → HCID 11792960, compound

HRID 2287375Notes

Reaction equation

HRID 2287375 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[N:23][CH:24]=1.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[N:23][CH:24]=1)(=[O:15])=[O:14]

Participants

6

Reactant 3

HCID 1049PyridineHCID 11801Dansyl chlorideHCID 793055-Amino-2-chloropyridine

Product 1

HCID 11792960HCID 11792960, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-dimethylamino-1-naphthalenesulphonyl chloride (1.35 g), 5-amino-2-chloropyridine (0.64 g), pyridine (0.4 g) and 4-dimethylaminopyridine (0.02 g) in dichloromethane (20 ml) was allowed to stand for three days. The solution was divided into two equal portions and each portion was applied to a separate silica gel Mega Bond Elut column. The columns were eluted with dichloromethane and the product-containing fractions were concentrated by evaporation. The residue was triturated with ether to give 5-(dimethylamino)-N-(2-chloro-5-pyridyl)-1-naphthalenesulphonamide (0.77 g); m.p. 145-146° C.; mass spectrum (+ve FAB, methanol/NBA): 362(M+H)+.

Workup

  1. washThe columns were eluted with dichloromethane
  2. concentrationthe product-containing fractions were concentrated by evaporation
  3. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-25a6cb6fd773478a9ef6f66104d11ee0
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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