Potassium Carbonate → HCID 59198935, compound

HRID 72728Notes

Reaction equation

HRID 72728 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][C:3]=1[N+:13]([O-])=O.[C:16]1([CH3:27])[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[NH:23][CH:24]=[CH:25][N:26]=2)[CH:17]=1.[C:28](=O)([O-])[O-:29].[K+].[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.C(O)(=O)C.CN(C)C(=O)C>[CH3:9][N:8]([CH3:10])[C:6]([C:5]1[CH:4]=[C:3]2[C:2](=[CH:12][CH:11]=1)[N:26]1[C:22]([C:18]3[CH:17]=[C:16]([CH3:27])[CH:21]=[CH:20][CH:19]=3)=[N:23][CH:24]=[C:25]1[C:28](=[O:29])[NH:13]2)=[O:7]

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 126227242-(3-Methylphenyl)-1H-imidazoleHCID 252393174-fluoro-N,N-dimethyl-3-nitrobenzamide

Product 1

HCID 59198935HCID 59198935, compoundYield 8.5%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoro-N,N-dimethyl-3-nitrobenzamide 1.21 g, 2-m-tolyl-1H-imidazole 600 mg, potassium carbonate 524 mg and N,N-dimethylacetamide 20 mL were mixed and stirred in nitrogen atmosphere for 12 hours at 100° C. After cooling off, the reaction liquid was diluted with ethyl acetate, and water was added to effect phase separation. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and from which the solvent was distilled off. Thus obtained crude product was dissolved in acetic acid 10 mL and water 10 mL, and to the solution 85% sodium hyposulfite 2.65 g was added, followed by 2 hours' heating under reflux. The reaction liquid was cooled with ice and neutralized with saturated sodium hydrogencarbonate solution, which was then extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. Distilling the solvent off, the resulting compound was mixed with 1,1′-carbonyldiimidazole 924 mg and 1,2-dichlorobenzene 30 mL, followed by heating under reflux for 10 hours in nitrogen, atmosphere. The reaction liquid was filtered to remove the insoluble matter, and then the solvent was distilled off. Purifying the product on silica gel column chromatography (chloroform:methanol=10:1) and P-TLC (chloroform:methanol=20:1) by the order stated, 112 mg of the title compound was obtained.

Workup

  1. temperatureAfter cooling off
  2. customthe reaction liquid
  3. additionwas added to effect phase separation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationfrom which the solvent was distilled off
  7. customThus obtained crude product
  8. waitfollowed by 2 hours
  9. temperature' heating
  10. temperatureunder reflux
  11. customThe reaction liquid
  12. extractionwas then extracted with ethyl acetate
  13. washThe extract was washed with saturated brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. distillationDistilling the solvent off, the resulting compound
  16. additionwas mixed with 1,1′-carbonyldiimidazole 924 mg and 1,2-dichlorobenzene 30 mL
  17. temperatureby heating
  18. temperatureunder reflux for 10 hours in nitrogen
  19. customThe reaction liquid
  20. filtrationwas filtered
  21. customto remove the insoluble matter
  22. distillationthe solvent was distilled off
  23. customPurifying the product on silica gel column chromatography (chloroform:methanol=10:1) and P-TLC (chloroform:methanol=20:1) by the order

Sources & evidence

ORD record
ord-901b9cb6f62a4f70812da2de3f9d1865
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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