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

HRID 1684563

반응식

HRID 1684563 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f0d04c2a21534de4970c9509173e77ce
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05641793

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