Formaldehyde → HCID 66718634, compound

HRID 1159484Notes

Reaction equation

HRID 1159484 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.[C:12](=[O:15])([O-])[O-].[K+].[K+].C=O.S(OC)(O[CH3:24])(=O)=O>CN(C=O)C.O.C(OCC)(=O)C>[OH:15][CH2:12][C:3]1[C:4]([C:8]([F:11])([F:10])[F:9])=[N:5][N:6]([CH3:7])[C:2]=1[O:1][CH3:24]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 6497Dimethyl SulfateHCID 11430Potassium Carbonate2×HCID 178481859HCID 178481859, compound

Product 1

HCID 66718634HCID 66718634, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 100 ml of DMF were suspended 16.6 g (0.10 mole) of the 5-hydroxy-1-methyl-3-trifluoromethylpyrazole synthesized in Reference Example 1 and 20.9 g (0.15 mole) of potassium carbonate. In this suspension being stirred at room temperature was placed 4.5 g (0.15 mole) of paraformaldehyde, followed by stirring at the same temperature for 1 hour. Then, 41.8 g (0.30 mole) of potassium carbonate was added. Thereto was dropwise added 25.2 g (0.20 mole) of dimethyl sulfate, followed by stirring at room temperature for 2 hours to give rise to a reaction. After the reaction, 200 ml of ethyl acetate and 200 ml of water were added. The organic layer, which appeared by phase separation, was separated. The aqueous layer was subjected to re-extraction with 50 ml of ethyl acetate. The two organic layers were combined and washed with 50 ml of water, 30 ml of a saturated aqueous ammonium chloride solution and 30 ml of a saturated aqueous sodium chloride solution in this order. The resulting organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 23.5 g (purity: 75.4%, yield: 84.3%) of a crude solution of title compound. The crude solution was subjected to vacuum distillation to obtain a title compound. The compound showed spectra identical to those indicated in Example 2.

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. stirringby stirring at room temperature for 2 hours
  3. customto give rise
  4. customto a reaction
  5. additionwere added
  6. customThe organic layer, which appeared by phase separation
  7. customwas separated
  8. extractionThe aqueous layer was subjected to re-extraction with 50 ml of ethyl acetate
  9. washwashed with 50 ml of water, 30 ml of a saturated aqueous ammonium chloride solution and 30 ml of a saturated aqueous sodium chloride solution in this order
  10. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e441913775b94d09bbaa5819c4decd86
Source dataset
uspto-grants-2010_10
Patent number
US07812175B2

Reaction notes

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