Trifluoroacetic acid → 3-(Octadecyloxy)-5-(phenylmethoxy)benzenamine

HRID 1757840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757840
CC(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:10]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:9]=1)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:23]([O:22][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 193890303-(Octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester

Produkt 1

HCID 193889513-(Octadecyloxy)-5-(phenylmethoxy)benzenamineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 28 g of 3-(octadecyloxy)-5-(phenylmethoxy)phenylcarbamic aciddimethylethyl ester and 76 ml of trifluoroacetic acid in 700 ml of methylene chloride was kept at room temperature for 2 hours. The solution was concentrated at reduced pressure and the residue was extracted with methylene chloride. The extract was washed with NaHCO3 solution, dried and concentrated to a solid which was dissolved in 1000 ml of ether.The solution was treated with 21 ml of 3N HCl in ethanol. The hydrochloridesalt which precipitated was filtered and treated with excess NaHCO3 toliberate the free base which was extracted with methylene chloride. The dried extract was concentrated at reduced pressure to give 20.4 g (89% yield, mp 57°-59°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzenamine.

Aufarbeitung

  1. concentrationThe solution was concentrated at reduced pressure
  2. extractionthe residue was extracted with methylene chloride
  3. washThe extract was washed with NaHCO3 solution
  4. customdried
  5. concentrationconcentrated to a solid which
  6. dissolutionwas dissolved in 1000 ml of ether
  7. additionThe solution was treated with 21 ml of 3N HCl in ethanol
  8. customThe hydrochloridesalt which precipitated
  9. filtrationwas filtered
  10. additiontreated with excess NaHCO3 toliberate the free base which
  11. extractionwas extracted with methylene chloride
  12. extractionThe dried extract
  13. concentrationwas concentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a405ccd63de445a5bc39a9cef22074ea
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446189

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