Cesium carbonate → HCID 86700754, compound

HRID 2272546Notes

Reaction equation

HRID 2272546 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:19]([C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[N:31]2[CH:35]=[C:34]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[N:33]=[CH:32]2)[NH:24][N:23]=1)([CH3:21])[CH3:20]>C(#N)C>[CH:19]([C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[N:31]2[CH:35]=[C:34]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)[N:33]=[CH:32]2)[N:24]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[N:23]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 178440405HCID 178440405, compound

Product 1

HCID 86700754HCID 86700754, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

4-Chloro-3-nitrobenzonitrile (331 mg) and cesium carbonate (700 mg) were added to a solution of compound (1a) (500 mg) in acetonitrile (5.5 mL), and the mixture was stirred under heating at 70° C. for 4 hours. After completion of the reaction, the reaction solution was allowed to standing still for cooling and partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and dried by the addition of anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was subjected to slurry washing (acetonitrile/methanol), thereby to obtain compound (10a) (470 mg, yield 64%) as a milky white solid.

Workup

  1. customAfter completion of the reaction
  2. temperaturefor cooling
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried by the addition of anhydrous sodium sulfate
  6. customAfter removal of the solvent
  7. customby evaporation
  8. washto slurry washing (acetonitrile/methanol)

Sources & evidence

ORD record
ord-c9b8b727a32d4cb28c3a8947c33a41f0
Source dataset
uspto-grants-2015_09
Patent number
US09120780B2

Reaction notes

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