Sodium hydride → N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-N-(1-methylethyl)-3-(trifluoromethyl)benzenesulfonamide

HRID 1719435

반응식

HRID 1719435 반응식
[CH:1]([NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:21][CH2:22][CH2:23][N:24]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[CH3:25]>CN(C)C=O>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([CH2:27][CH2:26][N:24]([CH3:25])[CH2:23][CH2:22][CH2:21][N:4]([CH:1]([CH3:3])[CH3:2])[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:7])=[O:6])[CH:33]=[CH:32][C:31]=1[O:34][CH3:35]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 23323137N-isopropyl-3-trifluoromethylbenzenesulfonamide

생성물 1

HCID 54053041N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-N-(1-methylethyl)-3-(trifluoromethyl)benzenesulfonamide수율 43.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-isopropyl-3-trifluoromethylbenzenesulfonamide (5.362 g, 0.02 mol) in dimethylformamide (30 mL) was treated with sodium hydride (60% in mineral oil), (0.802 g) and stirred for 2 hours. Then N-(3-chloropropyl)-3,4-dimethoxy-N-methylphenethylamine (5.436 g, 0.02 mol) was added and the reaction heated overnight. Filtration and removal of solvent provided the crude product (6.95 g). Column chromatography and high pressure liquid chromatography provided the pure product (4.35 g) as a gum. 1H NMR (CDCl3) 1.15 (d, 6, J=3.5H, Me2) 2.25 (s, 3, N--Me) 3.84 (d, 6, (OMe)2) 6.76 (m, 3, Ar) 7.25 (m, 3, Ar).

후처리

  1. temperaturethe reaction heated overnight
  2. filtrationFiltration and removal of solvent
  3. customprovided the crude product (6.95 g)

출처 및 근거

ORD 기록
ord-3bb134aecc594bbb99d7ed48eaac7667
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539426

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