4-Aminobiphenyl → Propynoic acid-biphenyl-4-ylamide

HRID 735025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735025
C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([OH:20])(=O)[C:17]#[CH:18].[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1.ClCCl.CO>ClCCl>[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=[CH:23][C:24]([NH:27][C:16](=[O:20])[C:17]#[CH:18])=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 71024-AminobiphenylHCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 21226129Dichloromethane methanol

Produkt 1

HCID 86060713Propynoic acid-biphenyl-4-ylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

9.38 g (45.5 mmol) of DCC are added batchwise to a solution of 2.89 g (41.36 mmol) of propynoic acid in 100 mL dichloromethane at −15° C. and stirred for 1 hour. Then a solution of 7 g (41.36 mmol) of biphenyl-4-ylamine-15° C. is added dropwise to 30 mL dichloromethane and stirred for 2 hours. After this time, the cooling bath is removed and the reaction mixture is allowed to come up to ambient temperature. 20 g of CELITE® filter aid is added to the reaction mixture and it is then filtered. The filtrate is evaporated down in vacuo. The residue is combined with acetonitrile and stirred. The suspension is filtered, the filtrate is evaporated down and the residue is stirred with petroleum ether and pentane. The solid is isolated by filtration. Yield: 5.5 g (60.1% of theory); C15H11NO (M=221.26); calc.: molecular ion peak (M+H)+: 222; found: molecular ion peak (M+H)+: 222; Rf value: 0.7 (silica gel, dichloromethane/methanol (10:1)).

Aufarbeitung

  1. stirringstirred for 2 hours
  2. customAfter this time, the cooling bath is removed
  3. customto come up to ambient temperature
  4. filtration20 g of CELITE® filter aid
  5. additionis added to the reaction mixture and it
  6. filtrationis then filtered
  7. customThe filtrate is evaporated down in vacuo
  8. stirringstirred
  9. filtrationThe suspension is filtered
  10. customthe filtrate is evaporated down
  11. stirringthe residue is stirred with petroleum ether and pentane
  12. customThe solid is isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d90c8611f864457ea1efd41c59d4cc27
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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