Dichloromethane → 2-(2'-Fluorophenyl)-(4s,5s)-diphenyl-4,5-dihydroimidazole

HRID 429507

Reaktionsgleichung

Reaktionsgleichung von HRID 429507
F[B-](F)(F)F.[F:6][CH2:7][CH2:8][C:9]1C=CC=C[C:10]=1[C:11](=N)[O-].[C:18]1([C@H:24]([NH2:33])[C@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH2:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ClCCl.C(N([CH2:42][CH3:43])CC)C>CCCCCC.O>[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:42]=1[C:43]1[NH:33][C@@H:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:26]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 6931238(1S,2S)-1,2-diphenylethane-1,2-diamineHCID 1317229942-Fluoro-ethylbenzimidate tetrafluoroborate

Produkt 1

HCID 207050562-(2'-Fluorophenyl)-(4s,5s)-diphenyl-4,5-dihydroimidazoleAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a 100 ml flask was charged 5.00 g imidate 7 (19.6 mmol, 1 eq.), 4.16 g (S,S)-1, 2-diphenylethylenediamine (19.6 mmol, 1 eq.), 50 ml dichloromethane, and 6.3 ml triethylamine (45.3 mmol, 2.3 eq.) in the order given. After stirring 4 hours at ambient temperature, the reaction mixture was poured into 50 ml water, the phases separated, and the aq. phase reextracted with dichloromethane. The combined methylene chloride layers were washed with 2% aq. ammonium chloride, dried with magnesium sulfate, filtered, and the filtrate evaporated in vacuo to give an oil. This oil was dissolved in 25 ml boiling hexane, cooled to 0°, filtered and air dried to give 4.80 g of 2-(2′-fluorophenyl)-(4S,5S)-diphenyl4,5-dihydroimidazole 8 (78%) as a colorless solid. M.p. 122-124° C.; MS (ES+): MH+317; 19F NMR (CDCl3)δ: −113.6 ppm.

Aufarbeitung

  1. customthe phases separated
  2. washThe combined methylene chloride layers were washed with 2% aq. ammonium chloride
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customto give an oil
  7. dissolutionThis oil was dissolved in 25 ml
  8. temperaturecooled to 0°
  9. filtrationfiltered
  10. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-ad7be0cd2bb9448b9ac540aa4a1fd5b4
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316620B1

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