Dansyl chloride → 5-(dimethylamino)-N-(5-bromo-3-methyl-2-pyridyl)-1-naphthalenesulphonamide

HRID 1684563

Reaction equation

HRID 1684563 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[C:24]([CH3:25])=[CH:23][C:22]([Br:26])=[CH:21][N:20]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[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[C:24]([CH3:25])=[CH:23][C:22]([Br:26])=[CH:21][N:20]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 11801Dansyl chlorideHCID 1379342-Amino-5-bromo-3-methylpyridine

Product 1

HCID 106457795-(dimethylamino)-N-(5-bromo-3-methyl-2-pyridyl)-1-naphthalenesulphonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 5-dimethylamino-1-naphthalenesulphonyl chloride (269.5 mg), 2-amino-5-bromo-3-methylpyridine (187 mg) and 4-dimethylaminopyridine (100 mg) in pyridine (5 ml) was heated at 85° C. for 18 hours. Volatile material was removed by evaporation and dichloromethane (50 ml) was added. Insoluble material was removed by filtration and the filtrate was concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), to give 5-(dimethylamino)-N-(5-bromo-3-methyl-2-pyridyl)-1-naphthalenesulphonamide as a foam (135) mg); NMR (CDCl3): 2.2(s, 3H), 2.9(s, 6H), 7.15 (d, 1H), (7.4-7.8(m, 4H), 8.4(d, 1H), 8.5(d, 2H); mass spectrum (+ve CI): 420 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation and dichloromethane (50 ml)
  2. additionwas added
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated by evaporation
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-f0d04c2a21534de4970c9509173e77ce
Source dataset
uspto-grants-1997_06
Patent number
US05641793

Linked notes

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