Hydrochloric Acid → HCID 86602532, compound

HRID 349790Notes

Reaction equation

HRID 349790 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].[Cl:11][C:12]1[CH:13]=[C:14](N=C=O)[CH:15]=[CH:16][C:17]=1[Cl:18].[H-].[Na+].Cl.C[N:26](C)[CH:27]=[O:28]>O>[Cl:11][C:12]1[CH:13]=[C:14]([C:1]23[CH2:8][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:9])[CH:3]([C:27]([NH2:26])=[O:28])[C:2]3=[O:10])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 76073,4-Dichlorophenyl isocyanateHCID 24758Sodium hydrideHCID 144686Bicyclo(3.2.1)octane-2,4-dione

Product 1

HCID 86602532HCID 86602532, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of bicyclo[3,2,1]octane-2,4-dione (0.34 g, 2.5 mmole), 3,4-dichlorophenyl isocyanate (0.94 g, 5 mmole), and 60% sodium hydride in mineral oil (0.11 g, 2.75 mmole) in dimethylformamide (100 mL) was stirred at 0° C. for 1 hour and 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 by chromatography on silica gel (40% dichloromethane/hexane) to give an oily solid as the expected product. The oily product was recrystallized from ethyl acetate/hexane to afford the title compound as a white solid, mp=146–148° C.; MS (−) ESI m/z=325 (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 by chromatography on silica gel (40% dichloromethane/hexane)

Sources & evidence

ORD record
ord-b9a7edd123974492849746c44e5a6dfc
Source dataset
uspto-grants-2007_02
Patent number
US07179943B2

Reaction notes

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