Water → 4-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalene-1-carboxamide

HRID 1873475ノート

反応式

HRID 1873475 の反応式
[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[CH:5][CH:4]=1.[CH3:16][Si:17]([CH3:21])([CH3:20])[CH2:18][NH2:19].Cl.CN(C)CCCN=C=NCC.O>ClCCl>[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([NH:19][CH2:18][Si:17]([CH3:21])([CH3:20])[CH3:16])=[O:15])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 874881-(Trimethylsilyl)methylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109783504-(bromomethyl)naphthalene-1-carboxylic Acid

生成物 1

HCID 580920724-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalene-1-carboxamide収率 32.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-(bromomethyl)naphthalen-1-carboxylic acid (7 g), 1-(trimethylsilyl)methylamine (2.7 g), N,N-dimethylaminopyridine (0.1 g) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (6.6 g) were dissolved in dichloromethane (30 ml), and stirred for 5 hours at room temperature. Water was added to the reaction mixture, and then organic layers, were separated and dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 4-(bromomethyl)-N-[(trimethylsilyl)methyl]naphthalene-1-carboxamide (3 g).

後処理

  1. customorganic layers, were separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtering the reaction mixture
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe resulting mixture was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-bbba0753b84f493ba611971039387096
出典データセット
uspto-grants-2012_11
特許番号
US08304371B2

反応ノート

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