Formaldehyde → HCID 66718660, compound

HRID 1159488Notes

Reaction equation

HRID 1159488 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.[CH2:12]=[O:13].C(#N)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[OH-].[K+]>[CH2:17]([O:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:12][OH:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 178481859HCID 178481859, compound

Product 1

HCID 66718660HCID 66718660, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent2×

Procedure

16.6 g (0.10 mole) of the 5-hydroxy-1-methyl-3-trifluoromethylpyrazole synthesized in Reference Example 1 was dissolved in 35.0 g (0.15 mole) of a 24% aqueous potassium hydroxide solution. To the solution being stirred at room temperature was dropwise added 9.7 g (0.12 mole) of a 37% formalin solution, followed by stirring at the same temperature for 1 hour. Then, there were added 70.0 g (0.3 mole) of a 24% aqueous potassium hydroxide solution and 100 ml of acetonitrile. Thereto was dropwise added 20.5 g (0.12 mole) of benzyl bromide at room temperature in 1 hour, followed by stirring at room temperature for 12 hours to give rise to a reaction. After the reaction, the organic layer which appeared by phase separation, was concentrated under reduced pressure to obtain 26.1 g (purity: 80.0%, yield: 73.1%) of a crude solution of title compound. The crude solution was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain a title compound as a light yellow transparent solution.

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. customat room temperature
  3. customin 1 hour
  4. stirringby stirring at room temperature for 12 hours
  5. customto give rise
  6. customto a reaction
  7. customAfter the reaction
  8. customthe organic layer which appeared by phase separation
  9. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-915042a9cfbb42d9b92a7184571b4dd4
Source dataset
uspto-grants-2010_10
Patent number
US07812175B2

Reaction notes

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