Hydrochloric Acid → HCID 86760840, Verbindung

HRID 2108509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2108509
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH2:27](Br)[CH:28]=[CH2:29].Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:29]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])[C:3](=[O:4])[C:2]([F:1])([F:17])[F:18])[CH:28]=[CH2:27]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 222927722,2,2-Trifluoro-N-[2-(2-iodo-5-methoxyphenyl)ethyl]acetamide

Produkt 1

HCID 86760840HCID 86760840, VerbindungAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-2-iodo-5-methoxyphenethylamine (23.8 g, 63.8 mmol) in toluene (425 mL) was sequentially treated with K2CO3 (12.4 g, 89.8 mmol), KOH (11.6 g, 207 mmol), n-Bu4NBr (2.2 g, 6.9 mmol) and allyl bromide (10.7 g, 89.8 mmol). The mixture was stirred at 80 C for 3.5 hours, cooled to 20 C, acidified with 10% aqueous HCl, separated and the aqueous phase extracted with ether (500 mL). The combined organic phases were washed with brine (200 mL), dried with Na2SO4 and concentrated to give 20.5 g of a brown oil. 1H NMR (400 MHz, CDCl3), mixture of rotamers d 7.67 (m, 1H), 6.80 (m, 1H), 6.57 (m, 1H), 5.9-5.6 (bm, 1H), 5.27 (m, 2H), 4.11 (d, J=6 Hz, 0.5H), 3.85 (d, J=6 Hz, 0.5H), 3.77 (m, 3H), 3.55 (m, 2H), 3.00 (m, 2H). MS calculated for C14H15F3INO2+H: 414, observed: 414.

Aufarbeitung

  1. temperaturecooled to 20 C
  2. customseparated
  3. extractionthe aqueous phase extracted with ether (500 mL)
  4. washThe combined organic phases were washed with brine (200 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0c0fb65c8a904de180c7476dae37dfe3
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514422B2

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