Hydrochloric Acid → HCID 11587867, compound

HRID 349788Notes

Reaction equation

HRID 349788 reaction equation
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:9])[CH2:3][C:2]2=[O:10].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15]([N:19]=[C:20]=[O:21])[CH:16]=[CH:17][CH:18]=1.[H-].[Na+].Cl>CN(C)C=O.O>[F:11][C:12]([F:22])([F:23])[C:13]1[CH:14]=[C:15]([NH:19][C:20]([CH:3]2[C:4](=[O:9])[CH:5]3[CH2:8][CH:1]([CH2:7][CH2:6]3)[C:2]2=[O:10])=[O:21])[CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 24758Sodium hydrideHCID 144686Bicyclo(3.2.1)octane-2,4-dione

Product 1

HCID 11587867HCID 11587867, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of bicyclo[3,2,1]octane-2,4-dione (0.27 g, 2.0 mmole), 3-(trifluoromethyl) phenyl isocyanate (0.55 ml, 4.0 mmole), and 60% sodium hydride in mineral oil (0.088 g, 2.2 mmole) in dimethylformamide (100 mL) was stirred at 0° C. for 1 hour and then heated at 45–50° C. under nitrogen for 24 hours. After cooling, the mixture was diluted with H2O and treated with 2N aqueous HCl until the mixture was clear. The clear solution was then extracted with dichloromethane. The organic layer was washed with H2O again, dried over anhydrous magnesium sulfate, and concentrated on a rotary evaporator. The residue was purified with by chromatography on silica gel (40% dichloromethane/hexane) to give a clear oily liquid as the expected product. The oily product was crystallized with ethyl acetate/hexane in a dry ice bath to afford the title compound as a white solid, mp=68–69° C.; MS (−) ESI m/z=324 (M−H)−.

Workup

  1. temperatureheated at 45–50° C. under nitrogen for 24 hours
  2. temperatureAfter cooling
  3. extractionThe clear solution was then extracted with dichloromethane
  4. washThe organic layer was washed with H2O again
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was purified with by chromatography on silica gel (40% dichloromethane/hexane)

Sources & evidence

ORD record
ord-e5b7db1f4e5b48a7b8f9b9681a2406e3
Source dataset
uspto-grants-2007_02
Patent number
US07179943B2

Reaction notes

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