Propanedioyl dichloride → HCID 49761343, compound

HRID 1878516Notes

Reaction equation

HRID 1878516 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][N:3]=1.[C:13]([Cl:19])(=O)[CH2:14][C:15]([Cl:17])=O>C(#N)C.O>[Cl:17][C:15]1[CH:14]=[C:13]([Cl:19])[N:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:6]=[C:2]2[N:1]=1

Participants

5

Reactant 2

HCID 74269Propanedioyl dichloride2×HCID 1366553-Amino-5-phenylpyrazole

Product 1

HCID 49761343HCID 49761343, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

There was dissolved, in acetonitrile (20 mL), 3-amino-5-phenyl-pyrazole (1.00 g, 6.28 mM) in an argon gas atmosphere, malonyl chloride (672 μL, 6.91 mM) was added to the resulting solution with ice-cooling and the mixture was stirred for 2 hours. To this reaction liquid, there was further added malonyl chloride (210 μL, 2.15 mM) followed by stirring the mixture for one hour. This reaction liquid was diluted with water and then extracted with ethyl acetate. The resulting extracts were combined, dried over anhydrous sodium sulfate and the solvent was then distilled off. After the addition of phosphoryl chloride (10 mL) to the resulting solid with ice-cooling, the resulting suspension was stirred for 4 hours, while refluxing the same with heating. The phosphoryl chloride was distilled off from the reaction liquid, the residue thus obtained was diluted with water and then extracted with methylene chloride. The extracts thus obtained were combined, dried over anhydrous sodium sulfate, the solvent was distilled off and then the resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:10) to thus give the title compound (168 mg, yield: 10%).

Workup

  1. temperaturecooling
  2. customTo this reaction liquid, there
  3. stirringby stirring the mixture for one hour
  4. customThis reaction liquid
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was then distilled off
  8. additionAfter the addition of phosphoryl chloride (10 mL) to the resulting solid with ice-
  9. temperaturecooling
  10. stirringthe resulting suspension was stirred for 4 hours
  11. temperaturewhile refluxing the same
  12. temperaturewith heating
  13. distillationThe phosphoryl chloride was distilled off from the reaction liquid
  14. customthe residue thus obtained
  15. extractionextracted with methylene chloride
  16. customThe extracts thus obtained
  17. dry with materialdried over anhydrous sodium sulfate
  18. distillationthe solvent was distilled off
  19. customthe resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:10)

Sources & evidence

ORD record
ord-2c0a530027d04dac9393e8d2c431b303
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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