Hydrochloric Acid → HCID 178427296, compound

HRID 1725115Notes

Reaction equation

HRID 1725115 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.[OH-].[Na+].[CH2:14]=O.[C:16]1([CH3:25])[CH:21]=[CH:20][C:19]([S:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.[Na+].Cl>C1(C)C=CC=CC=1.O>[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:14][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:25])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 2723791Sodium p-toluenesulfinateHCID 178481859HCID 178481859, compound

Product 1

HCID 178427296HCID 178427296, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5-Hydroxy-1-methyl-3-trifluoromethylpyrazole (1.7 g (10 mmol)) synthesized in Reference Example 1 and 0.6 g (15 mmol) of sodium hydroxide were dissolved in 10 mL of toluene. While stirring the resulting solution at room temperature, 1.7 g of paraformaldehyde was charged thereto, followed by stirring at the same temperature for 24 hours. Furthermore, 1.8 g (10 mmol) of sodium p-toluenesulfinate was charged thereto at room temperature, and the obtained mixture was stirred for 8 hours. After the reaction, 5.0 g (50 mmol) of 35% hydrochloric acid was added dropwise thereto, 30 mL of water was further added, and the precipitated crystal was collected by filtration, washed twice with 5 mL of water and dried by a hot air drier to obtain 3.0 g (yield: 88.2%) of the title compound as a pale yellow crystal. The 1H-NMR spectrum agreed with that of Example 6.

Workup

  1. stirringby stirring at the same temperature for 24 hours
  2. stirringat room temperature, and the obtained mixture was stirred for 8 hours
  3. additionwas added dropwise
  4. filtrationthe precipitated crystal was collected by filtration
  5. washwashed twice with 5 mL of water
  6. customdried by a hot air drier

Sources & evidence

ORD record
ord-c1663d098e114e1db618a9602c2b59b7
Source dataset
uspto-grants-2009_02
Patent number
US07488831B2

Reaction notes

Loading…