Hydrochloric Acid → N-[11-(3-fluoro-4-methoxy-phenyl)-11-oxo-undecyl]acetamide

HRID 2306466

Reaktionsgleichung

Reaktionsgleichung von HRID 2306466
C(Cl)(=O)C(Cl)=O.[C:7]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)(=[O:9])[CH3:8].C(NCCCCCCCCCCC(Cl)=O)(=O)C.[F:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[O:48][CH3:49].[Cl-].[Al+3].[Cl-].[Cl-].Cl>CN(C=O)C.C(Cl)Cl.O>[F:41][C:42]1[CH:47]=[C:46]([C:21](=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:7](=[O:9])[CH3:8])[CH:45]=[CH:44][C:43]=1[O:48][CH3:49]

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 675762-FluoroanisoleHCID 45408511-Acetamidoundecanoic acidHCID 6451240Aluminum(III) ChlorideHCID 1843429211-Acetylamino-undecanoyl chloride

Produkt 1

HCID 18434110N-[11-(3-fluoro-4-methoxy-phenyl)-11-oxo-undecyl]acetamideAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.5 ml of oxalyl chloride is added to a solution of 1.2 g of 11-acetylamino-undecanoic acid and 5 drops of DMF in 15 ml of methylene chloride at 0° C. and the mixture is stirred at RT for 3 hrs. The solution of the 11-acetylamino-undecanoyl chloride is treated under argon with 0.6 g of 2-fluoroanisole, cooled to −15° C. and treated with 1.4 g of aluminium chloride. After 2 hrs. at −15° C. the mixture is left to warm to room temperature overnight. The solution is treated with 15 ml of 1M hydrochloric acid at 0° C. and then with 20 ml of water. The organic phase is separated and washed with 1M hydrochloric acid, with water and with saturated sodium bicarbonate solution, dried and concentrated. 1.8 g of N-[11-(3-fluoro-4-methoxy-phenyl)-11-oxo-undecyl]acetamide are obtained.

Aufarbeitung

  1. temperaturecooled to −15° C.
  2. waitAfter 2 hrs
  3. waitat −15° C. the mixture is left
  4. temperatureto warm to room temperature overnight
  5. customThe organic phase is separated
  6. washwashed with 1M hydrochloric acid, with water and with saturated sodium bicarbonate solution
  7. customdried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-84ac9039dd8d4cddb08ba3c2cbfb5fac
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441177B1

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