2-Methyl-2-butanol → HCID 178453672、化合物

HRID 1108888

反応式

HRID 1108888 の反応式
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=1[O-:20].C([O-])(O)=O.[Na+].C(O)(CC)(C)C>C(Cl)Cl>[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=1[O-:20])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

参加物

6

反応物 4

HCID 64052-Methyl-2-butanolHCID 88478Chloride 2-chloropyridinium 1-oxideHCID 187201N-BOC-ethylenediamineHCID 516892Sodium Bicarbonate

生成物 1

HCID 178453672HCID 178453672、化合物収率 89.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of mono-Boc-1,2-ethylenediamine (5.83 g, 36.39 mmole), 2-chloropyridine-N-oxide hydrochloride (7.25 g, 43.67 mmole), NaHCO3 (15.29 g, 182 mmole), and tert-amyl alcohol (36 mL) was heated at reflux. After 47 hr, the dark brown mixture was cooled, diluted with CH2Cl2 (100 mL), and suction filtered to remove insoluble materials. The filtrate was concentrated and reconcentrated from toluene. Silica gel chromatography (10% MeOHICHCl3) gave impure title compound (8.23 g, 89%) as a yellow solid which was used without further purification: TLC (10% MeOH/CHCl3) Rf 0.42; 1H NMR (250, CDCl3) δ 8.16 (dd, J=6.5, 1.3 Hz, 1 H), 7.05-7.30 (m, 2 H), 6.68 (br d, J=8.6 Hz, 1 H), 6.50-6.65 (m, 1 H), 5.70-5.95 (m, 1 H), 3.25-3.60 (m, 4 H), 1.44 (s, 9 H); MS (ES) m/e 254 (M+H)+.

後処理

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe dark brown mixture was cooled
  4. filtrationfiltered
  5. customto remove insoluble materials
  6. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-1fe06105063e4fd9a0ff14d6fb54cead
出典データセット
uspto-grants-2000_05
特許番号
US06069158

関連ノート

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