Hydrochloric Acid → HCID 178527394, compound

HRID 1725116Notes

Reaction equation

HRID 1725116 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[OH-].[Na+].[CH2:19]=O.[C:21]1([S:27]([O-:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na+].Cl>O.C1(C)C=CC=CC=1>[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[C:3]=1[CH2:19][S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:29])=[O:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 2723840Benzenesulfinic acid, sodium saltHCID 178516151HCID 178516151, compound

Product 1

HCID 178527394HCID 178527394, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

5-Hydroxy-1-phenyl-3-trifluoromethylpyrazole (2.3 g (10 mmol)) synthesized in Reference Example 2 and 0.6 g (15 mmol) of sodium hydroxide were dissolved in 10 mL of water. While stirring the resulting solution at room temperature, 1.7 g (20 mmol) of a 35% formalin solution was added dropwise thereto, followed by stirring at the same temperature for 1 hour. Subsequently, 1.6 g (10 mmol) of sodium benzenesulfinate was charged thereto at room temperature, and the obtained mixture was stirred for 2 hours. After the reaction, 6.0 g (60 mmol) of 35% hydrochloric acid was added dropwise thereto, and the toluene layer obtained from an extraction operation performed twice with 20 mL of toluene was washed with 10 mL of water and then with 10 mL of saturated brine and dried over anhydrous sodium sulfate. Thereafter, toluene was removed by distillation under reduced pressure to obtain 3.4 g (yield: 88.1%) of the title compound as a viscous material. This viscous material was left standing at room temperature for 2 days and thereby crystallized.

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. stirringat room temperature, and the obtained mixture was stirred for 2 hours
  3. additionwas added dropwise
  4. washwas washed with 10 mL of water
  5. dry with materialwith 10 mL of saturated brine and dried over anhydrous sodium sulfate
  6. customThereafter, toluene was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-6103c74737834fea84d9f98c10dc4236
Source dataset
uspto-grants-2009_02
Patent number
US07488831B2

Reaction notes

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