Water → HCID 21924532, Verbindung

HRID 1269121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269121
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([N:15]([CH2:25][CH:26]=[CH2:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:13]=[CH2:14].N1C=CC=CC=1.O>C(Cl)(Cl)Cl>[CH2:25]([N:15]([CH2:12][CH:13]=[CH2:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH:26]=[CH2:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21924501HCID 21924501, Verbindung

Produkt 1

HCID 21924532HCID 21924532, VerbindungAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

4-Toluene-sulphonyl chloride (12.5 g, 0.066 mol) was added slowly to a stirred solution of 8-diallylaminooctan-1-ol (10.0 g, 0.044 mol) and pyridine (7.0 g, 0.088 mol) in chloroform (100 cm3) at 0° C. After 24 h, water (100 cm3) was added and the solution washed with dilute hydrochloric acid (20%, 100 cm3), sodium carbonate solution (100 cm3), water (100 cm3), dried (MgSO4) and concentrated to a yellow oil which was purified by column chromatography [silica gel, 4% diethyl ether in hexane eluting to DCM:ethanol 10:1] to yield the desired product (6.7 g, yield 40%).

Aufarbeitung

  1. washthe solution washed with dilute hydrochloric acid (20%, 100 cm3), sodium carbonate solution (100 cm3), water (100 cm3)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to a yellow oil which
  4. customwas purified by column chromatography [silica gel, 4% diethyl ether in hexane eluting to DCM:ethanol 10:1]

Quellen und Nachweise

ORD-Eintrag
ord-dcd70aeaff9e478f9a8144daf5a1f2f5
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199167B2

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