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Sodium Hydroxide → N-(4-methoxybenzyl)-N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amine

HRID 68622
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HRID 68622 반응식
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH:12]=O.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1.C(O[BH-](O[C:36](=[O:38])[CH3:37])OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:12][C:8]2[N:7]([CH2:6][O:38][CH2:36][CH2:37][Si:2]([CH3:1])([CH3:14])[CH3:3])[CH:11]=[CH:10][N:9]=2)[CH2:12][C:8]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[CH:11]=[CH:10][N:9]=2)=[CH:20][CH:19]=1
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참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 136002351-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehyde

생성물 1

HCID 67163648N-(4-methoxybenzyl)-N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amine

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 1-({[2-(trimethylsilyl)ethyloxy]methyl}-1H-imidazole-2-carboaldehyde (CAS Registry Number: 101226-42-0, 1.5 g) and {[4-(methyloxy)phenyl]methyl}amine (0.39 mL) in dichloromethane (containing 1% acetic acid) (10 mL), sodium triacetoxyborohydride (1.91 g) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was added by an aqueous 1 N sodium hydroxide solution and then extracted with dichloromethane. The extract thus obtained was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=1:0:0→10:1:0→10:1:0.1) to obtain the title compound (1.71 g) having the following physical properties.

후처리

  1. extractionextracted with dichloromethane
  2. extractionThe extract thus
  3. customobtained
  4. washwas washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=1:0:0→10:1:0→10:1:0.1)

출처 및 근거

ORD 기록
ord-7bcec049879541f8b4961276d5227d2e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822459B2

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