2-Methyl-2-butanol → HCID 178453672, Verbindung

HRID 1108888

Reaktionsgleichung

Reaktionsgleichung von HRID 1108888
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 178453672HCID 178453672, VerbindungAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1fe06105063e4fd9a0ff14d6fb54cead
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06069158

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