Hydrochloric Acid → HCID 178427294, compound

HRID 1725119Notes

Reaction equation

HRID 1725119 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]2[CH:17]=[C:16]([OH:18])[N:15]([CH3:19])[N:14]=2)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].[OH-].[Na+].[CH2:22]=O.[C:24]1([CH3:33])[CH:29]=[CH:28][C:27]([S:30]([O-:32])=[O:31])=[CH:26][CH:25]=1.[Na+].Cl>C(O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]([C:13]2[C:17]([CH2:22][S:30]([C:27]3[CH:28]=[CH:29][C:24]([CH3:33])=[CH:25][CH:26]=3)(=[O:32])=[O:31])=[C:16]([OH:18])[N:15]([CH3:19])[N:14]=2)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 2723791Sodium p-toluenesulfinateHCID 178481746HCID 178481746, compound

Product 1

HCID 178427294HCID 178427294, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(3,5-Dinitrophenyl)-5-hydroxy-1-methylpyrazole (0.65 g (2.5 mmol)) synthesized in Reference Example 4 and 0.15 g (3.8 mmol) of sodium hydroxide were dissolved in 5 mL of ethanol. While stirring the resulting solution at room temperature, 0.5 g (5.5 mmol) of a 35% formalin solution was added dropwise thereto, followed by stirring at the same temperature for 1 hour. Subsequently, 0.45 g (2.5 mmol) of sodium p-toluenesulfinate was charged thereto at room temperature, and the obtained mixture was stirred for 2 hours. After the reaction, 2.5 g (25 mmol) of 35% hydrochloric acid was added dropwise thereto, 15 mL of water was further added, and the precipitated crystal was collected by filtration, washed twice with 10 mL of water and dried by a hot air drier to obtain 0.9 g (yield: 89.3%) of the title compound as a brown crystal.

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. filtrationthe precipitated crystal was collected by filtration
  5. washwashed twice with 10 mL of water
  6. customdried by a hot air drier

Sources & evidence

ORD record
ord-f9e0fe24622d42f5846d02159d00d565
Source dataset
uspto-grants-2009_02
Patent number
US07488831B2

Reaction notes

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