4-Toluenesulfonyl chloride → HCID 3090868, Verbindung

HRID 1456885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1456885
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N([CH2:17][CH3:18])CC)C.[CH2:19]([N:26]([CH2:30][CH2:31][NH2:32])[CH2:27][CH2:28][NH2:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.C(OCC)(=O)C.CCOCC>[CH2:19]([N:26]([CH2:30][CH2:31][NH:32][S:7]([C:4]1[CH:5]=[CH:6][C:17]([CH3:18])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:27][CH2:28][NH:29][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

7

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10081318Benzylbis(2-aminoethyl)amine

Produkt 1

HCID 3090868HCID 3090868, VerbindungAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 141.2 g (0.741 mol) of p-toluenesulfonyl chloride in 250 ml of dichloromethane with 110 ml (0.8 mol) of triethylamine was added dropwise 68.0 g (0.352 mol) of 4-benzyl-1,4,7-triazaheptane in 75 ml of dichloromethane. After 2 hours, the solution was washed three times with water at pH 9, and the organic phase was dried with sodium sulfate and filtered. Evaporation gave an oil which was dissolved in about 450 ml of ethyl acetate. The solution was diluted with 200 ml of ether and left to stand at room temperature for 24 hours. The mixture was further diluted with about 50 ml of ether and refrigerated for another day. The product crystallized in massive prisms which were collected by filtration and dried under vacuum at 40° C. for 6 hours, yielding in the first crop 140 g (0.279 mol) of a colorless solid; melting point 87°-91° C. Mass spectrum (CI): m/e 502 (M+H) and 500 (M-H).

Aufarbeitung

  1. washthe solution was washed three times with water at pH 9
  2. dry with materialthe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. customEvaporation
  5. customgave an oil which
  6. waitleft
  7. waitto stand at room temperature for 24 hours
  8. waitrefrigerated for another day
  9. customThe product crystallized in massive prisms which
  10. filtrationwere collected by filtration
  11. customdried under vacuum at 40° C. for 6 hours

Quellen und Nachweise

ORD-Eintrag
ord-05e0a095278a49aab62ca64710bc6402
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05846519

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