Dodecanoyl chloride → HCID 53713524, Verbindung

HRID 1418827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1418827
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH:9](O)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH3:3].C(N([CH2:24][CH3:25])CC)C.[C:26](Cl)(=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(Cl)Cl>[O:38]=[C:26]([N:7]([CH2:8][CH2:9][CH2:10][N:11]([C:26](=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:24][CH3:25])[CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH2:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Komponenten

5

Edukt 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 537171762,14-Dimethyl-2,6,10,14-tetraazapentadecan-8-OL

Produkt 1

HCID 53713524HCID 53713524, VerbindungAusbeute 31,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,14-Dimethyl-8-hydroxy-2,6,10,14-tetrazapentadecane (17 g, 0.067 mol) synthesized in accordance with the method described in DE2616411, triethylamine (13 g, 0.13 mol), and methylene chloride (200 ml) were placed in a 500-ml four-necked round flask, and the mixture was cooled on ice. Dodecanoylchloride (29 g, 0.13 mol) was added dropwise over 1 hour to the flask while the contents of the flask were stirred under nitrogen. The mixture was stirred for 24 more hours at room temperature. The solid which precipitated was removed by filtration, after which water was added for washing. Methylene chloride was removed from the organic phase under reduced pressure. The residue was purified by column chromatography (packed with Kieselgel 60 (product of Merck), eluent: chloroform/methanol=7:1 (v/v)) to obtain 12.3 g of 4,8-bis(1-oxododecyl)-1,11-di(dimethylamino)-4,8-diazaundecane. Yield: 30 wt %.

Aufarbeitung

  1. customwere placed in a 500-ml four-necked round flask
  2. temperaturethe mixture was cooled on ice
  3. stirringThe mixture was stirred for 24 more hours at room temperature
  4. customThe solid which precipitated
  5. customwas removed by filtration
  6. additionafter which water was added
  7. washfor washing
  8. customMethylene chloride was removed from the organic phase under reduced pressure
  9. customThe residue was purified by column chromatography (packed with Kieselgel 60 (product of Merck), eluent: chloroform/methanol=7:1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-5daeb68281e64495afb8ee056dd26a2c
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05885955

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