Water → HCID 67061319, compound

HRID 602383Notes

Reaction equation

HRID 602383 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[NH2:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:16]=[C:15]([CH3:25])[CH:14]=1.C(N(CC)C(C)C)(C)C.O>S(Cl)(Cl)=O.C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:16]=[C:15]([CH3:25])[CH:14]=1)=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1128551H-Pyrazol-5-amine, 3-methyl-1-(4-methylphenyl)-HCID 6216403-Iodo-4-methylbenzoic acid

Product 1

HCID 67061319HCID 67061319, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

3-Iodo-4-methylbenzoic acid (1.00 g, 3.89 mmol) was dissolved in thionyl chloride (12.5 mL) and was stirred at 80° C. for 1.75 hours, then thionyl chloride was evaporated under reduced pressure. The reaction mixture was dissolved in methylene chloride (10.0 mL) and the solution was added with a solution of 5-amino-3-methyl-1-(p-tolyl)pyrazole (0.728 g, 3.89 mmol) and N,N-diisopropylethylamine (0.678 mL, 3.89 mmol) in methylene chloride (10.0 mL), followed by stirring at room temperature overnight. After the reaction mixture was added with water and extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, saturated aqueous ammonium chloride solution and water, followed by drying over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain 3-iodo-4-methyl-N-[5-methyl-2-(p-tolyl)-2H-pyrazol-3-yl]benzamide (1.44 g, 86%).

Workup

  1. customthionyl chloride was evaporated under reduced pressure
  2. dissolutionThe reaction mixture was dissolved in methylene chloride (10.0 mL)
  3. stirringby stirring at room temperature overnight
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, saturated aqueous ammonium chloride solution and water
  6. dry with materialby drying over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-f7d70882243c4ebe972aa05f12360632
Source dataset
uspto-grants-2011_03
Patent number
US07906522B2

Reaction notes

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