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

HRID 1684563

反応式

HRID 1684563 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-f0d04c2a21534de4970c9509173e77ce
出典データセット
uspto-grants-1997_06
特許番号
US05641793

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