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

HRID 429507

Reaction equation

HRID 429507 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ad7be0cd2bb9448b9ac540aa4a1fd5b4
Source dataset
uspto-grants-2001_11
Patent number
US06316620B1

Linked notes

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