1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22013909, Verbindung

HRID 2416945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2416945
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:22]([C:25]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]([CH3:34])[CH3:33])[C:26]=1[NH2:27])([CH3:24])[CH3:23].[Br:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](O)=[O:44]>CN(C=O)C>[Br:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([NH:27][C:26]1[C:25]([CH:22]([CH3:24])[CH3:23])=[CH:31][CH:30]=[CH:29][C:28]=1[CH:32]([CH3:34])[CH3:33])=[O:44]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 32484DiisopropylanilineHCID 757711-HydroxybenzotriazoleHCID 5482758-Bromooctanoic acid

Produkt 1

HCID 22013909HCID 22013909, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

WSC (1.05 g 5.5 mmols) and HOBt (743 mg, 5.5 mmols) were added to a DMF (15 ml) solution of 2,6-diisopropylaniline (886 mg, 5 mmols) and 8-bromooctanoic acid (1.67 g, 7.5 mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with ether. The organic layer was washed with water, 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. Then, the residue was purified through silica gel column chromatography (developer:hexane/acetone=5/1), and the resulting crystals were recrystallized from other-hexane to obtain 720 mg (yield: 38%) of 8-bromo-N-(2,6-diisopropylphenyl) octanamide as colorless needle-like crystals.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ether
  2. washThe organic layer was washed with water, 1 N HCl
  3. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThen, the residue was purified through silica gel column chromatography (developer:hexane/acetone=5/1)
  6. customthe resulting crystals were recrystallized from other-hexane

Quellen und Nachweise

ORD-Eintrag
ord-bfa327d10ec84fde9be1e5bc002bda92
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825223B2

Notizen zur Reaktion

Wird geladen…