Formaldehyde → HCID 66718904, compound

HRID 1159493Notes

Reaction equation

HRID 1159493 reaction equation
[C:1]([C:3]1[CH:7]=[C:6]([OH:8])[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=1)#[N:2].[CH2:15]=[O:16].C(#N)C.Cl[CH:21]([F:23])[F:22]>[OH-].[K+]>[C:1]([C:3]1[C:7]([CH2:15][OH:16])=[C:6]([O:8][CH:21]([F:23])[F:22])[N:5]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 6372ChlorodifluoromethaneHCID 178510261HCID 178510261, compound

Product 1

HCID 66718904HCID 66718904, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent2×

Procedure

18.5 g (0.10 mole) of the 3-cyano-5-hydroxy-1-phenylpyrazole synthesized in Reference Example 4 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. Therein was blown 17.3 g (0.20 mole) of chlorodifluoromethane at room temperature in 2 hours, followed by stirring at room temperature for 2 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 24.6 g (purity: 70.6%, yield: 65.5%) of a crude solution of title compound. The crude solution was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain a title compound as white crystals.

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. customat room temperature
  3. customin 2 hours
  4. stirringby stirring at room temperature for 2 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-1a3c36433c0141bdb618bf7f3fde378b
Source dataset
uspto-grants-2010_10
Patent number
US07812175B2

Reaction notes

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