Formaldehyde → HCID 117839336, compound

HRID 1477597Notes

Reaction equation

HRID 1477597 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.C=O.[CH2:12](N(CC)CC)C.[C:19]1([CH3:39])[CH:24]=[CH:23][C:22]([S:25]([O:28]S(C2C=CC(C)=CC=2)(=O)=O)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>N12CCCN=C1CCCCC2.C(OCC)(=O)C.O1CCCC1>[CH3:39][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:28][CH2:12][N:5]2[CH:4]=[C:3]([C:2]([F:9])([F:8])[F:1])[CH:7]=[N:6]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 77773Toluene-p-sulphonic anhydrideHCID 127777954-(Trifluoromethyl)-1H-pyrazole

Product 1

HCID 117839336HCID 117839336, compound

Reagents, catalysts & solvents 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (2 mL) of 4-(trifluoromethyl)-1H-pyrazole, 1,8-diazabicyclo[5.4.0]undec-7-ene (10.9 μL, 0.07 mmol) and paraformaldehyde (43.8 mg, 1.46 mmol) were added at room temperature and the resultant mixture was stirred at 60° C. for 12 hours and at room temperature for 1 day. The reaction solution was filtered and triethylamine (153 μL, 1.10 mmol) and p-toluenesulfonic acid anhydride (286 mg, 0.88 mmol) were added to the filtrate, following by stirring the resultant mixture for 30 minutes. After completion of the reaction, saturated sodium carbonate aqueous solution was added to the reaction solution and extraction with ethyl acetate from the resultant mixture was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained residue, ethyl acetate was added and the resultant mixture was filtered and concentrated under reduced pressure to obtain a crude product (232 mg) of the title compound.

Workup

  1. filtrationThe reaction solution was filtered
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionTo the obtained residue, ethyl acetate was added
  5. filtrationthe resultant mixture was filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-154274099f6a422c85ac211d405c44c4
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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