11-Bromoundecanoic acid → N3(CH2)10C(O)Cl

HRID 1062943

Reaktionsgleichung

Reaktionsgleichung von HRID 1062943
BrCCCCCCCCCCC(O)=O.[N-]=[N+]=[N-].[Na+].[N:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=O)=[N+:20]=[N-:21].C(Cl)(=O)C([Cl:38])=O>CN(C=O)C.[Cl-].[Na+].O.C1C=CC=CC=1.CCOCC>[N:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([Cl:38])=[O:34])=[N+:20]=[N-:21]

Komponenten

9

Edukt 4

HCID 1781211-Bromoundecanoic acidHCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 45409411-Azidoundecanoic acid

Produkt 1

HCID 22283452N3(CH2)10C(O)Cl

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a glass reaction vessel, 10.6 grams (40 mmol) of 11-Bromoundecanoic acid was dissolved in 225 milliliters DMF and 26 grams (400 mmol) sodium azide was added. The resulting stirred mixture was heated to 80° C. for 16 h, and then the reaction mixture was worked up with ether and brine. The ether layer was dried (MgSO4), filtered, and concentrated to 9.5 grams of N3(CH2)10C(O)OH as a pale yellow oil which was used without purification. In a glass reaction vessel, the N3(CH2)10C(O)OH was dissolved in 120 milliliters benzene and 12.7 grams (100 mmol) oxalyl chloride was added. The reaction was allowed to stir for 20 h, at which time the volatiles were removed in vacuo. The resulting residue was dissolved in pentane and filtered in a nitrogen atmosphere to remove solids. Concentration of the filtrate afforded N3(CH2)10C(O)Cl as a clear, yellow oil.

Aufarbeitung

  1. dry with materialThe ether layer was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated to 9.5 grams of N3(CH2)10C(O)OH as a pale yellow oil which
  4. customwas used without purification
  5. customIn a glass reaction vessel
  6. stirringto stir for 20 h, at which time the volatiles
  7. customwere removed in vacuo
  8. dissolutionThe resulting residue was dissolved in pentane
  9. filtrationfiltered in a nitrogen atmosphere
  10. customto remove solids

Quellen und Nachweise

ORD-Eintrag
ord-e0100f53ab5b4481a43da17cbfb2e00c
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06963007B2

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