Hydrochloric Acid → N-Allyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

HRID 1010783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010783
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH2:26](Br)[CH:27]=[CH2:28].Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:28]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])[C:3](=[O:4])[C:2]([F:16])([F:1])[F:17])[CH:27]=[CH2:26]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 22292821N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

Produkt 1

HCID 24773729N-Allyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamineAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-2-iodo-4-chlorophenethylamine (0.94 g, 2.4 mmol) in toluene (25 mL) was treated with K2CO3 (0.43 g, 3.12 mmol), KOH (0.40 g, 7.2 mmol), n-Bu4NBr (0.077 g, 0.24 mmol) and allyl bromide (0.43 g, 3.6 mmol) sequentially. The mixture was stirred at 80 C for 3.5 hours, cooled to 20 C and acidified with 10% aqueous HCl. The phases were separated, the aqueous phase extracted with ether (100 mL), the combined organic phases were washed with brine (50 mL), dried with Na2SO4 and concentrated to give 0.76 g of a clear oil. MS calculated for C13H12ClF3INO+H: 418, observed: 418.

Aufarbeitung

  1. temperaturecooled to 20 C
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with ether (100 mL)
  4. washthe combined organic phases were washed with brine (50 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9c572701d6264b7b9822bbf6ae66a1e7
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977329B2

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